Double Ring Expansion Strategy for Fused 3‑Benzazepines: Alternative Synthesis of the Dolby–Weinreb Enamine
A double ring expansion strategy for constructing fused 3-benzazepines is described. The oxidative ring expansion of spiroamine compounds with N-chlorosuccinimide and subsequent ring expansion of the resulting ketiminium ion intermediates with trimethylsilyldiazomethane afforded fused 3-benzazepines...
Saved in:
| Published in | Journal of organic chemistry Vol. 87; no. 24; pp. 16947 - 16951 |
|---|---|
| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
16.12.2022
Amer Chemical Soc |
| Subjects | |
| Online Access | Get full text |
Cover
Loading…
| Abstract | A double ring expansion strategy for constructing fused 3-benzazepines is described. The oxidative ring expansion of spiroamine compounds with N-chlorosuccinimide and subsequent ring expansion of the resulting ketiminium ion intermediates with trimethylsilyldiazomethane afforded fused 3-benzazepines in a one-pot operation. Importantly, the Dolby–Weinreb enamine, which is a key synthetic intermediate for harringtonine alkaloids, cephalotaxines, can be accessed from commercial materials in only two steps using our developed method. |
|---|---|
| AbstractList | A double ring expansion strategy for constructing fused 3-benzazepines is described. The oxidative ring expansion of spiroamine compounds with N-chlorosuccinimide and subsequent ring expansion of the resulting ketiminium ion intermediates with trimethylsilyldiazomethane afforded fused 3-benzazepines in a one-pot operation. Importantly, the Dolby-Weinreb enamine, which is a key synthetic intermediate for harringtonine alkaloids, cephalotaxines, can be accessed from commercial materials in only two steps using our developed method. A double ring expansion strategy for constructing fused 3-benzazepines is described. The oxidative ring expansion of spiroamine compounds with -chlorosuccinimide and subsequent ring expansion of the resulting ketiminium ion intermediates with trimethylsilyldiazomethane afforded fused 3-benzazepines in a one-pot operation. Importantly, the Dolby-Weinreb enamine, which is a key synthetic intermediate for harringtonine alkaloids, cephalotaxines, can be accessed from commercial materials in only two steps using our developed method. A double ring expansion strategy for constructing fused 3-benzazepines is described. The oxidative ring expansion of spiroamine compounds with N-chlorosuccinimide and subsequent ring expansion of the resulting ketiminium ion intermediates with trimethylsilyldiazomethane afforded fused 3-benzazepines in a one-pot operation. Importantly, the Dolby-Weinreb enamine, which is a key synthetic intermediate for harringtonine alkaloids, cephalotaxines, can be accessed from commercial materials in only two steps using our developed method.A double ring expansion strategy for constructing fused 3-benzazepines is described. The oxidative ring expansion of spiroamine compounds with N-chlorosuccinimide and subsequent ring expansion of the resulting ketiminium ion intermediates with trimethylsilyldiazomethane afforded fused 3-benzazepines in a one-pot operation. Importantly, the Dolby-Weinreb enamine, which is a key synthetic intermediate for harringtonine alkaloids, cephalotaxines, can be accessed from commercial materials in only two steps using our developed method. |
| Author | Arisawa, Mitsuhiro Sako, Makoto Aoyama, Hiroshi Murai, Kenichi Saito, Keigo |
| AuthorAffiliation | Graduate School of Pharmaceutical Sciences |
| AuthorAffiliation_xml | – name: Graduate School of Pharmaceutical Sciences |
| Author_xml | – sequence: 1 givenname: Keigo surname: Saito fullname: Saito, Keigo – sequence: 2 givenname: Hiroshi surname: Aoyama fullname: Aoyama, Hiroshi – sequence: 3 givenname: Makoto orcidid: 0000-0002-4268-7002 surname: Sako fullname: Sako, Makoto – sequence: 4 givenname: Mitsuhiro orcidid: 0000-0002-7937-670X surname: Arisawa fullname: Arisawa, Mitsuhiro email: murai@phs.osaka-u.ac.jp – sequence: 5 givenname: Kenichi orcidid: 0000-0002-1689-6492 surname: Murai fullname: Murai, Kenichi email: arisaw@phs.osaka-u.ac.jp |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/36475678$$D View this record in MEDLINE/PubMed |
| BookMark | eNqNkU9rFDEYh4NU7LZ69iY5CjLb_NlkMt7qdqtCQbCKx5DJvFNTZpM1yWi3p36F4jfsJzFlpx6Egrkk8D5PQn6_A7TngweEXlIyp4TRI2PT_DLYObOELWrxBM2oYKSSDVnsoRkhjFWcSb6PDlK6JGUJIZ6hfS4LLGs1Q-EkjO0A-LPzF3h1tTE-ueDxeY4mw8UW9yHi0zFBh_ndze078NfmGjbOQ3qLj4cM0ZvsfgI-3_r8HZJLOPS4nPBJGNrt3c3vb-B8hBavvFkX7Tl62pshwYtpP0RfT1dflh-qs0_vPy6PzyrDmyZXousZo5YaTrnsuCU1pZIKqrpasa6m1i4ISCVtpxpiewkNI0z2C9XWhtDG8EP0enfvJoYfI6Ss1y5ZGAbjIYxJs7okoUpATUFfTejYrqHTm-jWJm71Q0gFeLMDfkEb-mQdeAt_sRKqagSVhN7nSwut_p9eulzyC34ZRp-LKnaqjSGlCL2207zU4QZNib5vXZfWdWldT60X7-gf7-G5x43pS7vBWGoc0qP0H4l9vnQ |
| CitedBy_id | crossref_primary_10_1002_chem_202302919 crossref_primary_10_1016_j_tet_2025_134524 crossref_primary_10_1021_acs_joc_4c02431 crossref_primary_10_1002_ajoc_202400652 |
| Cites_doi | 10.1055/s-0030-1258306 10.1021/ja00842a030 10.1021/acs.orglett.9b01433 10.1021/acs.orglett.7b04008 10.1021/jo00867a026 10.1002/anie.201508804 10.1021/ol501933h 10.1021/jo00290a011 10.1021/acs.orglett.5b02159 10.1039/D0OB01822H 10.1016/j.clml.2013.03.017 10.1002/ajoc.202100543 10.1021/ol1003324 10.1002/anie.202012664 10.1021/acs.orglett.6b00233 10.1021/ol017114f 10.1021/ar50089a003 10.1002/adsc.201600985 10.1021/jo00796a027 10.1039/c2np20037f 10.1021/acs.orglett.8b00675 10.1039/C5SC02913A 10.1002/asia.201901799 10.1021/acs.orglett.9b04228 10.1021/jo050143+ 10.1002/ajoc.201900318 10.1021/acs.orglett.1c01323 10.1021/ja00775a062 10.1039/c39760000505 10.1039/c5sc02913a 10.1039/d0ob01822h |
| ContentType | Journal Article |
| Copyright | 2022 American Chemical Society |
| Copyright_xml | – notice: 2022 American Chemical Society |
| DBID | AAYXX CITATION 17B 1KM AHQBO BLEPL DTL EGQ CGR CUY CVF ECM EIF NPM 7X8 |
| DOI | 10.1021/acs.joc.2c02475 |
| DatabaseName | CrossRef Web of Knowledge Index Chemicus Web of Science - Science Citation Index Expanded - 2022 Web of Science Core Collection Science Citation Index Expanded Web of Science Primary (SCIE, SSCI & AHCI) Medline MEDLINE MEDLINE (Ovid) MEDLINE MEDLINE PubMed MEDLINE - Academic |
| DatabaseTitle | CrossRef Web of Science MEDLINE Medline Complete MEDLINE with Full Text PubMed MEDLINE (Ovid) MEDLINE - Academic |
| DatabaseTitleList | Web of Science MEDLINE MEDLINE - Academic |
| Database_xml | – sequence: 1 dbid: NPM name: PubMed url: https://proxy.k.utb.cz/login?url=http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed sourceTypes: Index Database – sequence: 2 dbid: 1KM name: Index Chemicus url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/woscc/search-with-editions?editions=WOS.IC sourceTypes: Enrichment Source Index Database |
| DeliveryMethod | fulltext_linktorsrc |
| Discipline | Chemistry |
| EISSN | 1520-6904 |
| EndPage | 16951 |
| ExternalDocumentID | 36475678 000895160100001 10_1021_acs_joc_2c02475 c953004242 |
| Genre | Research Support, Non-U.S. Gov't Journal Article |
| GrantInformation_xml | – fundername: Japan Society for the Promotion of Science (JSPS) KAKENHI; Ministry of Education, Culture, Sports, Science and Technology, Japan (MEXT); Japan Society for the Promotion of Science; Grants-in-Aid for Scientific Research (KAKENHI) grantid: T17K082100 – fundername: Grants-in-Aid for Scientific Research; Ministry of Education, Culture, Sports, Science and Technology, Japan (MEXT); Japan Society for the Promotion of Science; Grants-in-Aid for Scientific Research (KAKENHI) grantid: 22H05366 – fundername: AMED grantid: JP21am0101084; JP22ama121054 |
| GroupedDBID | --- -DZ -~X .K2 29L 4.4 55A 5RE 5VS 7~N 85S 8W4 AABXI ABFLS ABFRP ABMVS ABPPZ ABPTK ABQRX ABUCX ACGFO ACGFS ACJ ACNCT ACS ADHLV AEESW AENEX AFEFF AGXLV ALMA_UNASSIGNED_HOLDINGS AQSVZ BAANH CS3 D0L DU5 EBS ED~ F5P GGK GNL IH2 IH9 IHE JG~ LG6 P2P PZZ ROL RXW TAE TAF TN5 UI2 UKR UPT VF5 VG9 VQA W1F WH7 XFK XSW YQT YZZ ZCA 53G AAHBH AAYXX ABBLG ABJNI ABLBI ACBEA AHGAQ CITATION CUPRZ 17B 1KM BLEPL DTL GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED GROUPED_WOS_WEB_OF_SCIENCE CGR CUY CVF ECM EIF NPM YIN 7X8 |
| ID | FETCH-LOGICAL-a399t-5df221c1a3136d3c071161518d782d71cc40e686cd890cf6e92026f48b7a019a3 |
| IEDL.DBID | ACS |
| ISICitedReferencesCount | 5 |
| ISICitedReferencesURI | https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000895160100001 |
| ISSN | 0022-3263 1520-6904 |
| IngestDate | Fri Jul 11 09:03:38 EDT 2025 Wed Feb 19 02:25:03 EST 2025 Wed Jun 18 05:14:51 EDT 2025 Fri Aug 29 16:11:21 EDT 2025 Tue Jul 01 02:43:13 EDT 2025 Thu Apr 24 23:04:12 EDT 2025 Wed Dec 21 09:30:45 EST 2022 |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 24 |
| Keywords | REARRANGEMENT AMINES CEPHALOTAXINE |
| Language | English |
| License | https://doi.org/10.15223/policy-029 https://doi.org/10.15223/policy-037 https://doi.org/10.15223/policy-045 |
| LinkModel | DirectLink |
| LogoURL | https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg |
| MergedId | FETCHMERGED-LOGICAL-a399t-5df221c1a3136d3c071161518d782d71cc40e686cd890cf6e92026f48b7a019a3 |
| Notes | KAKEN ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
| ORCID | 0000-0002-7937-670X 0000-0002-4268-7002 0000-0002-1689-6492 0000-0001-7915-8975 |
| PMID | 36475678 |
| PQID | 2755580029 |
| PQPubID | 23479 |
| PageCount | 5 |
| ParticipantIDs | webofscience_primary_000895160100001 webofscience_primary_000895160100001CitationCount acs_journals_10_1021_acs_joc_2c02475 pubmed_primary_36475678 proquest_miscellaneous_2755580029 crossref_citationtrail_10_1021_acs_joc_2c02475 crossref_primary_10_1021_acs_joc_2c02475 |
| ProviderPackageCode | CITATION AAYXX |
| PublicationCentury | 2000 |
| PublicationDate | 2022-12-16 |
| PublicationDateYYYYMMDD | 2022-12-16 |
| PublicationDate_xml | – month: 12 year: 2022 text: 2022-12-16 day: 16 |
| PublicationDecade | 2020 |
| PublicationPlace | WASHINGTON |
| PublicationPlace_xml | – name: WASHINGTON – name: United States |
| PublicationTitle | Journal of organic chemistry |
| PublicationTitleAbbrev | J ORG CHEM |
| PublicationTitleAlternate | J. Org. Chem |
| PublicationYear | 2022 |
| Publisher | American Chemical Society Amer Chemical Soc |
| Publisher_xml | – name: American Chemical Society – name: Amer Chemical Soc |
| References | ref9/cit9c ref9/cit9b ref9/cit9a ref11/cit11 ref16/cit16 ref10/cit10a ref10/cit10b ref10/cit10c ref9/cit9i ref9/cit9h ref8/cit8 ref9/cit9g ref9/cit9f ref2/cit2 ref9/cit9e ref9/cit9d ref5/cit5b ref5/cit5c ref5/cit5a ref12/cit12 ref15/cit15 ref3/cit3b ref3/cit3c ref3/cit3a ref4/cit4 ref6/cit6a ref1/cit1 ref6/cit6b ref6/cit6c ref7/cit7 Xiao, TB (WOS:000340517200045) 2014; 16 TSE, I (WOS:A1976BY05300016) 1976 Murai, K (WOS:000430898200048) 2018; 20 WEINREB, SM (WOS:A1975AA53000030) 1975; 97 Jamali, MF (WOS:000512726700001) 2020; 15 Xiao, T (WOS:000361087200053) 2015; 17 DOLBY, LJ (WOS:A1972O019300027) 1972; 37 WEINSTEIN, B (WOS:A1976BH68700026) 1976; 41 Yuan, TR (WOS:000600480900001) 2021; 60 Ieawsuwa, W (WOS:000476036400001) 2019; 8 Ma, BC (WOS:000229321100047) 2005; 70 Zhang, ZW (WOS:000276562600001) 2010; 12 Jeon, H (WOS:000710557200001) 2021; 10 AUERBACH, J (WOS:A1972N650500062) 1972; 94 Sakai, T (WOS:000661126700058) 2021; 23 FANG, FG (WOS:A1990CM52200011) 1990; 55 Zhu, CL (WOS:000513082700011) 2020; 22 Stockerl, S (WOS:000473116000029) 2019; 21 WEINREB, SM (WOS:A1975AB91800003) 1975; 8 Abdelkafi, H (WOS:000306216200002) 2012; 29 Morita, M (WOS:000286479200010) 2010 Gini, A (WOS:000391810000018) 2016; 358 Zhang, ZW (WOS:000426013600039) 2018; 20 Hayashi, Y (WOS:000368835300003) 2016; 7 Koseki, Y (WOS:000174441700005) 2002; 4 Murai, K (WOS:000372664600025) 2016; 18 Bisag, GD (WOS:000588548000003) 2020; 18 Kantarjian, HM (WOS:000325509600002) 2013; 13 Xia, AJ (WOS:000369852200039) 2016; 55 |
| References_xml | – ident: ref9/cit9d doi: 10.1055/s-0030-1258306 – ident: ref5/cit5b doi: 10.1021/ja00842a030 – ident: ref9/cit9e doi: 10.1021/acs.orglett.9b01433 – ident: ref10/cit10c doi: 10.1021/acs.orglett.7b04008 – ident: ref6/cit6b doi: 10.1021/jo00867a026 – ident: ref9/cit9f doi: 10.1002/anie.201508804 – ident: ref9/cit9g doi: 10.1021/ol501933h – ident: ref6/cit6c doi: 10.1021/jo00290a011 – ident: ref9/cit9h doi: 10.1021/acs.orglett.5b02159 – ident: ref12/cit12 doi: 10.1039/D0OB01822H – ident: ref2/cit2 doi: 10.1016/j.clml.2013.03.017 – ident: ref3/cit3a doi: 10.1002/ajoc.202100543 – ident: ref10/cit10b doi: 10.1021/ol1003324 – ident: ref3/cit3b doi: 10.1002/anie.202012664 – ident: ref8/cit8 doi: 10.1021/acs.orglett.6b00233 – ident: ref10/cit10a doi: 10.1021/ol017114f – ident: ref5/cit5c doi: 10.1021/ar50089a003 – ident: ref9/cit9a doi: 10.1002/adsc.201600985 – ident: ref4/cit4 doi: 10.1021/jo00796a027 – ident: ref1/cit1 doi: 10.1039/c2np20037f – ident: ref15/cit15 doi: 10.1021/acs.orglett.8b00675 – ident: ref16/cit16 doi: 10.1039/C5SC02913A – ident: ref9/cit9c doi: 10.1002/asia.201901799 – ident: ref11/cit11 doi: 10.1021/acs.orglett.9b04228 – ident: ref7/cit7 doi: 10.1021/jo050143+ – ident: ref9/cit9i doi: 10.1021/acs.orglett.9b04228 – ident: ref9/cit9b doi: 10.1002/ajoc.201900318 – ident: ref3/cit3c doi: 10.1021/acs.orglett.1c01323 – ident: ref5/cit5a doi: 10.1021/ja00775a062 – ident: ref6/cit6a doi: 10.1039/c39760000505 – volume: 22 start-page: 809 year: 2020 ident: WOS:000513082700011 article-title: Regioselective Synthesis of 3-Trifluoromethylpyrazole by Coupling of Aldehydes, Sulfonyl Hydrazides, and 2-Bromo-3,3,3-trifluoropropene publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.9b04228 – volume: 23 start-page: 4391 year: 2021 ident: WOS:000661126700058 article-title: Gold(I)-Catalyzed Cyclization-3-Aza-Cope-Mannich Cascade and Its Application to the Synthesis of Cephalotaxine publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.1c01323 – volume: 18 start-page: 1314 year: 2016 ident: WOS:000372664600025 article-title: Oxidative Rearrangement via in Situ Generated N-Chloroamine: Synthesis of Fused Tetrahydroisoquinolines publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.6b00233 – volume: 60 start-page: 4070 year: 2021 ident: WOS:000600480900001 article-title: Stereoselective Gold(I)-Catalyzed Vinylcyclopropanation via Generation of a Sulfur-Substituted Vinyl Carbene Equivalent publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.202012664 – volume: 94 start-page: 7172 year: 1972 ident: WOS:A1972N650500062 article-title: TOTAL SYNTHESIS OF CEPHALOTAXINE publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY – volume: 13 start-page: 530 year: 2013 ident: WOS:000325509600002 article-title: Homoharringtonine/Omacetaxine Mepesuccinate: The Long and Winding Road to Food and Drug Administration Approval publication-title: CLINICAL LYMPHOMA MYELOMA & LEUKEMIA doi: 10.1016/j.clml.2013.03.017 – volume: 4 start-page: 885 year: 2002 ident: WOS:000174441700005 article-title: A formal total synthesis of (±)-cephalotaxine using sequential N-acyliminium ion reactions publication-title: ORGANIC LETTERS doi: 10.1021/ol017114f – volume: 17 start-page: 4332 year: 2015 ident: WOS:000361087200053 article-title: Ag(I)-Catalyzed Three-Component Reaction of 2-Alkynylbenzaldehydes, Amines, and Diazo Compounds publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.5b02159 – start-page: 4221 year: 2010 ident: WOS:000286479200010 article-title: Facile Synthesis of 1-Methyl-1H-benzo[b]azepines from 1-Methylquinolinium Iodides and Diazo(trimethylsilyl)methylmagnesium Bromide publication-title: SYNTHESIS-STUTTGART doi: 10.1055/s-0030-1258306 – volume: 37 start-page: 3691 year: 1972 ident: WOS:A1972O019300027 article-title: STUDIES OF SYNTHESIS OF CEPHALOTAXINE .1. publication-title: JOURNAL OF ORGANIC CHEMISTRY – volume: 8 start-page: 158 year: 1975 ident: WOS:A1975AB91800003 article-title: SYNTHESIS OF CEPHALOTAXUS ALKALOIDS publication-title: ACCOUNTS OF CHEMICAL RESEARCH – volume: 70 start-page: 4528 year: 2005 ident: WOS:000229321100047 article-title: An alternative synthesis of Dolby-Weinreb enamine en route to cephalotaxine publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo050143+ – start-page: 505 year: 1976 ident: WOS:A1976BY05300016 article-title: PHOTOCHEMICAL PREPARATION OF DIHYDRO-PYRROLO[2,1-B][3]BENZAZEPINES - CEPHALOTAXUS ALKALOID SYNTHON publication-title: JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS – volume: 29 start-page: 845 year: 2012 ident: WOS:000306216200002 article-title: Natural products from Cephalotaxus sp.: chemical diversity and synthetic aspects publication-title: NATURAL PRODUCT REPORTS doi: 10.1039/c2np20037f – volume: 15 start-page: 757 year: 2020 ident: WOS:000512726700001 article-title: Ag-Catalyzed Trifluoromethylative Ring Expansion of Isatins and Isatin Ketimines with Trifluorodiazoethane publication-title: CHEMISTRY-AN ASIAN JOURNAL doi: 10.1002/asia.201901799 – volume: 8 start-page: 1441 year: 2019 ident: WOS:000476036400001 article-title: Scandium(III)-Triflate-Catalyzed Pinacol-Pinacolone Rearrangement and Cyclization of 1,2-Diaryl-1,2-Ethanediol: A Versatile Synthesis of 1-Aryl-2,3-Dihydro-1H-3-Benzazepines publication-title: ASIAN JOURNAL OF ORGANIC CHEMISTRY doi: 10.1002/ajoc.201900318 – volume: 7 start-page: 866 year: 2016 ident: WOS:000368835300003 article-title: Pot economy and one-pot synthesis publication-title: CHEMICAL SCIENCE doi: 10.1039/c5sc02913a – volume: 10 start-page: 3052 year: 2021 ident: WOS:000710557200001 article-title: Recent Total Syntheses of Cephalotaxine-Type Alkaloids (2016-2021) publication-title: ASIAN JOURNAL OF ORGANIC CHEMISTRY doi: 10.1002/ajoc.202100543 – volume: 20 start-page: 1050 year: 2018 ident: WOS:000426013600039 article-title: Asymmetric Formal Synthesis of (-)-Cephalotaxine via Palladium-Catalyzed Enantioselective Tsuji Allylation publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.7b04008 – volume: 21 start-page: 4535 year: 2019 ident: WOS:000473116000029 article-title: Mild, Metal-Free Oxidative Ring-Expansion Approach for the Synthesis of Benzo[b]azepines publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.9b01433 – volume: 16 start-page: 4232 year: 2014 ident: WOS:000340517200045 article-title: Metal-Free Visible-Light Induced Cross-Dehydrogenative Coupling of Tertiary Amines with Diazo Compounds publication-title: ORGANIC LETTERS doi: 10.1021/ol501933h – volume: 358 start-page: 4049 year: 2016 ident: WOS:000391810000018 article-title: Synthesis of 3-Benzazepines by Metal-Free Oxidative C-H Bond Functionalization-Ring Expansion Tandem Reaction publication-title: ADVANCED SYNTHESIS & CATALYSIS doi: 10.1002/adsc.201600985 – volume: 97 start-page: 2503 year: 1975 ident: WOS:A1975AA53000030 article-title: TOTAL SYNTHESIS OF CEPHALOTAXUS ALKALOIDS - CEPHALOTAXINE, CEPHALOTAXINONE, AND DEMETHYLCEPHALOTAXINONE publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY – volume: 18 start-page: 8793 year: 2020 ident: WOS:000588548000003 article-title: Sulfoxonium ylides: simple compounds with chameleonic reactivity publication-title: ORGANIC & BIOMOLECULAR CHEMISTRY doi: 10.1039/d0ob01822h – volume: 55 start-page: 831 year: 1990 ident: WOS:A1990CM52200011 article-title: NEW ROUTES TO FUNCTIONALIZED BENZAZEPINE SUBSTRUCTURES - A NOVEL TRANSFORMATION OF AN ALPHA-DIKETONE THIOAMIDE INDUCED BY TRIMETHYL PHOSPHITE publication-title: JOURNAL OF ORGANIC CHEMISTRY – volume: 41 start-page: 875 year: 1976 ident: WOS:A1976BH68700026 article-title: SYNTHETIC APPROACH TO CEPHALOTAXINE SKELETON publication-title: JOURNAL OF ORGANIC CHEMISTRY – volume: 20 start-page: 2333 year: 2018 ident: WOS:000430898200048 article-title: Oxidative Rearrangement of Secondary Amines Using Hypervalent Iodine(III)-Reagent publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.8b00675 – volume: 12 start-page: 1649 year: 2010 ident: WOS:000276562600001 article-title: A Facile Total Synthesis of Hainanensine via an Unusual Rearrangement-Annulation Cascade publication-title: ORGANIC LETTERS doi: 10.1021/ol1003324 – volume: 55 start-page: 1441 year: 2016 ident: WOS:000369852200039 article-title: Metal-Free Ring-Expansion Reaction of Six-membered Sulfonylimines with Diazomethanes: An Approach toward Seven-Membered Enesulfonamides publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201508804 |
| SSID | ssj0000555 |
| Score | 2.4324203 |
| Snippet | A double ring expansion strategy for constructing fused 3-benzazepines is described. The oxidative ring expansion of spiroamine compounds with... |
| Source | Web of Science |
| SourceID | proquest pubmed webofscience crossref acs |
| SourceType | Aggregation Database Index Database Enrichment Source Publisher |
| StartPage | 16947 |
| SubjectTerms | Alkaloids Benzazepines Chemistry Chemistry, Organic Molecular Structure Physical Sciences Science & Technology |
| Title | Double Ring Expansion Strategy for Fused 3‑Benzazepines: Alternative Synthesis of the Dolby–Weinreb Enamine |
| URI | http://dx.doi.org/10.1021/acs.joc.2c02475 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000895160100001 https://www.ncbi.nlm.nih.gov/pubmed/36475678 https://www.proquest.com/docview/2755580029 |
| Volume | 87 |
| WOS | 000895160100001 |
| WOSCitedRecordID | wos000895160100001 |
| hasFullText | 1 |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV3LTtwwFLUoLOiGV2kZSpGRWHSTMHYeznQ3DDNClcqCh2AX-RVpYJogkkHMrPgF1D_kS3rvJBMoAypRFpFjW7Lvtc-xr3VMyC6AZmISoZ1I-cbxA487yrSUI5Om8bQnhDYY0f11FB6e-T8vgosnseiXEXzO9qTO3ctMu1wDnIjgA1ngYSRwndXunDxNukEQ1MLgPPRqFZ-ZChCGdP4vDM1wy1dhaAI5veXysFY-USrEkyZX7rBQrh7P6jj-vzUrZKkinrRdesoqmbPpGlnsTO97-0Qy4NJqYOkxgBnt3sEsgRtptJKvHVFgt7Q3zK2h3uP9w75Nx3Jsr_HU_A_aHlT7ireWnoxSIJV5P6dZQuGLHmQDNXq8_3Nu--CrinZT-RuKrZOzXve0c-hU1zE4ElhM4QQm4ZxpJj3mhWBIICdIF1lkgGUYwbT2mzaMQrBuq6mT0LY4LPASP1JCApGU3mcyn2ap3SBUWSkF7kgbH55ItjTnQFx8ZnyjoihpkF3oqLgaTnk8iZRzFpeJOq56r0HcqRFjXUma480ag7cLfK8LXJdqHm9n3Zl6RQyGwDCKTG02zGMuUCMNw5kN8qV0l7oyVOMPAP-hAc_9p_6PlAs4La6CkV03CHtPtk7VNpQpKDbf1zdfyUeOg4HBG26R-eJmaL8BfyrU9mTk_AUijRVX |
| linkProvider | American Chemical Society |
| linkToHtml | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwlZ1Lb9NAEMdHbXpoLzwKlFCgi9QDF4fs-pneQkiUPiVoK3qz9mWpEOwKO4jklK-A-Ib9JMw4jltoKxXLB8v2rry7s57f7tj_BdhGp5mYJNROpDzjeL4rHGU6ypFJ27jaDUNtKKJ7eBQMT729M_9sCdqLf2HwIXLMKS-D-FfqAvwdnfuS6ZbQ6FVCfxlWEEUEDbe6veOrd6_v-7U-uAjcWsznRgbkjXT-tze6gZi3eqPS8wwewsf6mcsPTr62xoVq6ek_co7_U6hH8KDCUNad281jWLLpOqz2Fqu_PYEMyVqNLPuEro31f-I7g6bVWCVmO2HIumwwzq1h7uXs13ubTuXUXtA39DusO6pmGX9YdjxJETHz85xlCcMj9iEbqcnl7Pdne46Wq1g_ld8w2VM4HfRPekOnWpzBkcg0heObRAiuuXS5G2CzIqoQPPLIIHOYkGvttW0QBdjWnbZOAtsRONxLvEiFErFSus-gkWapfQ5MWSlDmp82Hm6R7GghEGM8bjyjoihpwjZWVFx1rjwu4-aCx_OTOq5qrwmtRVvGuhI4p3U2RncneFsnuJhre9x965uFccTYEBRUkanNxnksQlJMo-BmEzbmVlNnRtr8PtIAFuC6GdXXCcCQcGlMTKzdBH6f23pV2Ui0oHhxv7rZgtXhyeFBfLB7tL8Ja4L6B8c9eAmN4vvYvkKyKtTrsjP9AXyGHbg |
| linkToPdf | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwlV1JbxMxFH6CIgEX9iWsRuqBy6SxZw23kCYqW4UoEb2NvEql6UzETBDJqX8B8Q_7S3hv4gxLqVRGcxh5bMvLe36f_ezPAJtoNJ1xqQ4yFZkgikMRKNNXgXQ9E-owTbUhj-673WRnEr3ej_f9oTA6C4OFqDCnqnHik1bPjPMMA3yLwj-Xuis0WpY0vgiXyGlHU67BcO_X-BvHccsRLpKwJfQ5lQFZJF39aZFOwcx_WqTG-oyvw6Qtd7Pp5LA7r1VXL_-idPzfit2Aax6OssFKfm7CBVvcgivD9S1wt6FEhK2mln1AE8dG33DsoOU15kltFwwxLxvPK2tYeHL8_aUtlnJpZ7SX_gUbTP1q41fL9hYFQs3qoGKlY_jFtsupWpwc__hkD1CCFRsV8giT3YHJePRxuBP4SxoCidimDmLjhOCay5CHCXYvQhYCkTwziD1MyrWOejbJEuzzfk-7xPYFTvtclKlUIryU4V3YKMrC3gemrJQprVObCJ9M9rUQCGcibiKjssx1YBMbKvdKVuWN_1zwfBWoc996Heiu-zPXnuic7tuYnp3geZtgtuL4ODvqs7WA5NgR5FyRhS3nVS5SYk4jJ2cH7q0kp82MOPpjRAVYgd9Fqf1PQAyRLs2NCXN3gJ8n2tDXjcgL6gfna5uncPn99jh_-2r3zUO4KkhFOL7JI9iov8ztYwRYtXrS6NNPrssgOw |
| openUrl | ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Double+Ring+Expansion+Strategy+for+Fused+3-Benzazepines%3A+Alternative+Synthesis+of+the+Dolby%E2%80%93Weinreb+Enamine&rft.jtitle=Journal+of+organic+chemistry&rft.au=Saito%2C+Keigo&rft.au=Aoyama%2C+Hiroshi&rft.au=Sako%2C+Makoto&rft.au=Arisawa%2C+Mitsuhiro&rft.date=2022-12-16&rft.issn=0022-3263&rft.eissn=1520-6904&rft.volume=87&rft.issue=24&rft.spage=16947&rft.epage=16951&rft_id=info:doi/10.1021%2Facs.joc.2c02475&rft.externalDBID=n%2Fa&rft.externalDocID=10_1021_acs_joc_2c02475 |
| thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0022-3263&client=summon |
| thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0022-3263&client=summon |
| thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0022-3263&client=summon |