Palladium-catalyzed regioselective arylation of imidazo[1,2-b][1,2,4]triazine: synthesis of an alpha 2/3-selective GABA agonist
A convergent, practical, and efficient synthesis of 2',6-difluoro-5'-[3-(1-hydroxy-1-methylethyl)imidazo[1,2-b][1,2,4]triazin-7-yl]biphenyl-2-carbonitrile (1), an orally active GABA(A) alpha(2/3)-selective agonist, is described. The seven-step, chromatography-free synthesis was demonstrate...
Saved in:
| Published in | Journal of organic chemistry Vol. 70; no. 15; pp. 5938 - 5945 |
|---|---|
| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
United States
22.07.2005
|
| Subjects | |
| Online Access | Get full text |
Cover
Loading…
| Abstract | A convergent, practical, and efficient synthesis of 2',6-difluoro-5'-[3-(1-hydroxy-1-methylethyl)imidazo[1,2-b][1,2,4]triazin-7-yl]biphenyl-2-carbonitrile (1), an orally active GABA(A) alpha(2/3)-selective agonist, is described. The seven-step, chromatography-free synthesis was demonstrated on a multi-kilogram scale and utilized biaryl bromide 6 and imidazotriazine 22 as key intermediates. Biaryl bromide 6 was prepared via a highly selective aromatic bromination. The regioselective condensation of aminotriazine 15 with chloroacetaldehyde provided the desired imidazotriazine intermediate 22. A highly regioselective palladium-catalyzed arylation in the final step highlights the efficiency of the route. |
|---|---|
| AbstractList | A convergent, practical, and efficient synthesis of 2',6-difluoro-5'-[3-(1-hydroxy-1-methylethyl)imidazo[1,2-b][1,2,4]triazin-7-yl]biphenyl-2-carbonitrile (1), an orally active GABA(A) alpha(2/3)-selective agonist, is described. The seven-step, chromatography-free synthesis was demonstrated on a multi-kilogram scale and utilized biaryl bromide 6 and imidazotriazine 22 as key intermediates. Biaryl bromide 6 was prepared via a highly selective aromatic bromination. The regioselective condensation of aminotriazine 15 with chloroacetaldehyde provided the desired imidazotriazine intermediate 22. A highly regioselective palladium-catalyzed arylation in the final step highlights the efficiency of the route. |
| Author | Devine, Paul N Foster, Bruce S Limanto, John Gauthier, Jr, Donald R Szumigala, Jr, Ronald H Volante, R P Desmond, Richard A |
| Author_xml | – sequence: 1 givenname: Donald R surname: Gauthier, Jr fullname: Gauthier, Jr, Donald R email: donald_gauthier@merck.com organization: Department of Process Research, Merck Research Laboratories, Merck & Co. Inc., P.O. Box 2000, Rahway, NJ 07065, USA. donald_gauthier@merck.com – sequence: 2 givenname: John surname: Limanto fullname: Limanto, John – sequence: 3 givenname: Paul N surname: Devine fullname: Devine, Paul N – sequence: 4 givenname: Richard A surname: Desmond fullname: Desmond, Richard A – sequence: 5 givenname: Ronald H surname: Szumigala, Jr fullname: Szumigala, Jr, Ronald H – sequence: 6 givenname: Bruce S surname: Foster fullname: Foster, Bruce S – sequence: 7 givenname: R P surname: Volante fullname: Volante, R P |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/16018689$$D View this record in MEDLINE/PubMed |
| BookMark | eNpFkF1LwzAUhoNM3Ide-AekV4KwuJOk6Yd3c-gUBnqhVzJKmqZbRpvMphW2G_-6LRvu3LxweHjhfYaoZ6xRCF0TuCdAyWRjgUMIjJ-hAeEUcBCD30MDAEoxowHro6FzG2iPc36B-iQAEgVRPEC_76IoRKabEktRi2K3V5lXqZW2ThVK1vpHeaLaFaLW1ng293SpM7G3X2RMcbrsYuwv60qLvTbqwXM7U6-V065jhfFEsV0Lj04YPvXNp49TT6ys0a6-ROe5KJy6OuYIfT4_fcxe8OJt_jqbLrAkNIoxI6HMKUDKA5qHoKgP3cOPecxCygWRAeFhHhPIFZMZISIVWcoI-EDT1JdshG4PvdvKfjfK1UmpnVTtdqNs45IgavVFNG7BuwMoK-tcpfJkW-myVZAQSDrbyb_tlr05ljZpqbITedTL_gAxwXsa |
| CitedBy_id | crossref_primary_10_1246_cl_200475 crossref_primary_10_1002_chem_201905475 crossref_primary_10_1002_ejoc_201700356 crossref_primary_10_1002_anie_201201666 crossref_primary_10_1002_ajoc_201800203 crossref_primary_10_1021_jo1018574 crossref_primary_10_1016_j_biopsych_2008_01_021 crossref_primary_10_1126_science_1143373 crossref_primary_10_1016_j_tet_2013_05_100 crossref_primary_10_1016_j_tet_2009_10_015 crossref_primary_10_1039_c1cc10708a crossref_primary_10_1246_cl_2007_200 crossref_primary_10_1002_anie_201602483 crossref_primary_10_1021_jo301065s crossref_primary_10_1002_bio_4344 crossref_primary_10_1021_jacs_5b08707 crossref_primary_10_1016_j_ccr_2007_03_011 crossref_primary_10_1016_j_tet_2011_06_001 crossref_primary_10_1021_ja0679580 crossref_primary_10_1039_D3CS00282A crossref_primary_10_1002_ange_201201666 crossref_primary_10_1002_ange_201710377 crossref_primary_10_1016_j_jics_2021_100247 crossref_primary_10_1016_j_tetlet_2006_02_117 crossref_primary_10_1021_jm051200u crossref_primary_10_1021_acs_organomet_8b00720 crossref_primary_10_1039_D1CY00021G crossref_primary_10_1021_cr100346g crossref_primary_10_1039_C5CY02095F crossref_primary_10_1002_ange_200604369 crossref_primary_10_1002_adsc_201500391 crossref_primary_10_1002_ange_201602483 crossref_primary_10_1002_anie_200604369 crossref_primary_10_1021_tx400021f crossref_primary_10_1002_adsc_202101204 crossref_primary_10_1021_co300007a crossref_primary_10_1002_adsc_201301139 crossref_primary_10_1177_0269881109354928 crossref_primary_10_1021_acscatal_0c05533 crossref_primary_10_1021_ol101235f crossref_primary_10_1021_jo801675h crossref_primary_10_1002_anie_201710377 crossref_primary_10_1021_cr3002966 crossref_primary_10_1021_jo8026565 crossref_primary_10_1016_j_ccr_2009_07_023 crossref_primary_10_1021_cr0509760 |
| Cites_doi | 10.1021/jo016342k 10.1246/bcsj.71.467 10.1016/0301-0082(91)90036-Z 10.1021/jo972141y 10.1021/ja0259279 10.1021/ol015598+ 10.1016/S0040-4039(98)02043-7 10.1046/j.1440-1681.1999.03151.x 10.1021/ol000183u 10.1021/op970107f 10.1021/jo035184p 10.1016/0040-4039(96)01398-6 10.1002/1615-9314(20020901)25:13<847::AID-JSSC847>3.0.CO;2-2 10.1021/ol015850d 10.1021/ol034602+ 10.1021/ja0002058 10.1016/S0165-6147(99)01413-3 10.1021/ol0158866 10.1002/9783527612222 10.1021/jo00100a048 10.1021/ol027266q 10.2174/0929867003375380 10.1002/jhet.5570310226 10.1021/jo00239a027 |
| ContentType | Journal Article |
| DBID | CGR CUY CVF ECM EIF NPM AAYXX CITATION 7X8 |
| DOI | 10.1021/jo0507035 |
| DatabaseName | Medline MEDLINE MEDLINE (Ovid) MEDLINE MEDLINE PubMed CrossRef MEDLINE - Academic |
| DatabaseTitle | MEDLINE Medline Complete MEDLINE with Full Text PubMed MEDLINE (Ovid) CrossRef MEDLINE - Academic |
| DatabaseTitleList | 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: EIF name: MEDLINE url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/medline/basic-search sourceTypes: Index Database |
| DeliveryMethod | fulltext_linktorsrc |
| Discipline | Chemistry |
| EISSN | 1520-6904 |
| EndPage | 5945 |
| ExternalDocumentID | 10_1021_jo0507035 16018689 |
| Genre | Journal Article |
| GroupedDBID | --- -DZ -~X .GJ .K2 186 29L 4.4 53G 55A 5RE 5VS 6TJ 7~N 85S AABXI AAHBH AAYOK ABJNI ABMVS ABPPZ ABQRX ABUCX ACBEA ACGFO ACGFS ACJ ACNCT ACS ACTDY ADHLV AEESW AENEX AFEFF AGXLV AHGAQ AIDAL ALMA_UNASSIGNED_HOLDINGS ANTXH AQSVZ BAANH CGR CS3 CUPRZ CUY CVF D0L DU5 EBS ECM ED~ EIF EJD F5P GGK GNL IH2 IH9 IHE JG~ LG6 NHB NPM OHT P2P PZZ ROL RXW TAE TAF TN5 UI2 UKR UPT UQL VF5 VG9 VQA W1F WH7 XOL XSW YQJ YQT YZZ ZCA ZCG AAYXX ACRPL CITATION 7X8 |
| ID | FETCH-LOGICAL-c1289-317cf200b562f70e2407cf249593725a1c6157f910fe3cd11abadb310402bb4c3 |
| IEDL.DBID | ACS |
| ISSN | 0022-3263 |
| IngestDate | Sun Sep 29 07:34:16 EDT 2024 Fri Dec 06 00:46:01 EST 2024 Sat Sep 28 07:44:47 EDT 2024 |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 15 |
| Language | English |
| LinkModel | DirectLink |
| MergedId | FETCHMERGED-LOGICAL-c1289-317cf200b562f70e2407cf249593725a1c6157f910fe3cd11abadb310402bb4c3 |
| Notes | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
| PMID | 16018689 |
| PQID | 68035829 |
| PQPubID | 23479 |
| PageCount | 8 |
| ParticipantIDs | proquest_miscellaneous_68035829 crossref_primary_10_1021_jo0507035 pubmed_primary_16018689 |
| PublicationCentury | 2000 |
| PublicationDate | 2005-Jul-22 |
| PublicationDateYYYYMMDD | 2005-07-22 |
| PublicationDate_xml | – month: 07 year: 2005 text: 2005-Jul-22 day: 22 |
| PublicationDecade | 2000 |
| PublicationPlace | United States |
| PublicationPlace_xml | – name: United States |
| PublicationTitle | Journal of organic chemistry |
| PublicationTitleAlternate | J Org Chem |
| PublicationYear | 2005 |
| References | Kristensen J. (jo0507035b00013/jo0507035b00013_1) 2001; 3 Bettati M. (jo0507035b00005/jo0507035b00005_1) 2002; 156 Kondo Y. (jo0507035b00010/jo0507035b00010_1) 1999; 121 jo0507035b00038/jo0507035b00038_1 LeBlond C. R. (jo0507035b00035/jo0507035b00035_1) 2001; 3 Sakurai H. (jo0507035b00035/jo0507035b00035_2) 2002; 67 Sezen B. (jo0507035b00006/jo0507035b00006_4) 2003; 125 Li W. (jo0507035b00008/jo0507035b00008_1) 2003; 5 Zhang C. (jo0507035b00032/jo0507035b00032_2) 1999; 64 Arduengo A. J. (jo0507035b00032/jo0507035b00032_1) 1999; 32 Limanto J. (jo0507035b00026/jo0507035b00026_1) 2003; 5 Glover B. (jo0507035b00007/jo0507035b00007_3) 2003; 5 Chebib M. (jo0507035b00003/jo0507035b00003_2) 1999; 26 Sezen B. (jo0507035b00006/jo0507035b00006_5) 2003; 125 Pivsa-Art S. (jo0507035b00006/jo0507035b00006_1) 1998; 71 Sivilotti L. (jo0507035b00001/jo0507035b00001_1) 1991; 36 Osman A. N. (jo0507035b00021/jo0507035b00021_2) 1996; 35 Aoyagi Y. (jo0507035b00006/jo0507035b00006_3) 1992; 33 jo0507035b00011/jo0507035b00011_1 Carling W. R. (jo0507035b00004/jo0507035b00004_1) 2003; 42 Kondo Y. (jo0507035b00006/jo0507035b00006_2) 2000; 2 Park C.-H. (jo0507035b00029/jo0507035b00029_1) 2004; 6 (jo0507035b00017/jo0507035b00017_1) 1965; 30 Szumigala R. H. (jo0507035b00014/jo0507035b00014_1) 2004; 69 Ohta A. (jo0507035b00007/jo0507035b00007_1) 1990; 31 Mongin F. (jo0507035b00016/jo0507035b00016_1) 1996; 37 Larsen R. D. (jo0507035b00036/jo0507035b00036_1) 1994; 59 (jo0507035b00020/jo0507035b00020_1) 1994; 31 Okazawa T. (jo0507035b00007/jo0507035b00007_4) 2002; 124 Pfuller O. C. (jo0507035b00022/jo0507035b00022_1) 1998; 39 Littke A. F. (jo0507035b00031/jo0507035b00031_1) 2000; 122 McClure M. S. (jo0507035b00007/jo0507035b00007_2) 2001; 3 Caron S. (jo0507035b00013/jo0507035b00013_2) 1998; 63 Bettati M. (jo0507035b00027/jo0507035b00027_1) 2003; 67 Chen C. (jo0507035b00034/jo0507035b00034_1) 2003; 68 Ueda T. (jo0507035b00021/jo0507035b00021_1) 1964; 12 Ballistreri F. P. (jo0507035b00025/jo0507035b00025_1) 1988; 53 Bormann J. (jo0507035b00002/jo0507035b00002_1) 2000; 21 jo0507035b00033/jo0507035b00033_1 Armer R. (jo0507035b00003/jo0507035b00003_3) 2000; 7 Lane B. S. (jo0507035b00007/jo0507035b00007_5) 2004; 6 Rosso V. W. (jo0507035b00037/jo0507035b00037_1) 1997; 1 (jo0507035b00012/jo0507035b00012_1) 2002; 4 Chambers M. S. (jo0507035b00003/jo0507035b00003_1) 2003; 46 Deiterich F. (jo0507035b00009/jo0507035b00009_1) 1998 (jo0507035b00030/jo0507035b00030_1) 2002; 41 Li W. (jo0507035b00013/jo0507035b00013_3) 2002; 67 Colonge J. (jo0507035b00025/jo0507035b00025_2) 1947; 841 |
| References_xml | – volume: 841 start-page: 843 year: 1947 ident: jo0507035b00025/jo0507035b00025_2 publication-title: Bull. Soc. Chim. Fr. contributor: fullname: Colonge J. – volume: 67 start-page: 5397 year: 2002 ident: jo0507035b00013/jo0507035b00013_3 publication-title: J. Org. Chem. contributor: fullname: Li W. – volume: 32 start-page: 921 year: 1999 ident: jo0507035b00032/jo0507035b00032_1 publication-title: III Acc. Chem. Res. contributor: fullname: Arduengo A. J. – volume: 67 start-page: 2722 year: 2002 ident: jo0507035b00035/jo0507035b00035_2 publication-title: J. Org. Chem. doi: 10.1021/jo016342k contributor: fullname: Sakurai H. – volume: 71 start-page: 473 year: 1998 ident: jo0507035b00006/jo0507035b00006_1 publication-title: Bull. Chem. Soc. Jpn. doi: 10.1246/bcsj.71.467 contributor: fullname: Pivsa-Art S. – volume: 68 start-page: 2638 year: 2003 ident: jo0507035b00034/jo0507035b00034_1 publication-title: J. Org. Chem. contributor: fullname: Chen C. – volume: 46 start-page: 2240 year: 2003 ident: jo0507035b00003/jo0507035b00003_1 publication-title: J. Med. Chem. contributor: fullname: Chambers M. S. – volume: 4 start-page: 378 year: 2002 ident: jo0507035b00012/jo0507035b00012_1 publication-title: J. Org. Lett. – volume: 30 start-page: 305 year: 1965 ident: jo0507035b00017/jo0507035b00017_1 publication-title: J. J. Org. Chem. – volume: 67 start-page: 2003093272 year: 2003 ident: jo0507035b00027/jo0507035b00027_1 publication-title: PCT Int. Appl. contributor: fullname: Bettati M. – ident: jo0507035b00011/jo0507035b00011_1 – volume: 36 start-page: 92 year: 1991 ident: jo0507035b00001/jo0507035b00001_1 publication-title: Prog. Neurobiol. doi: 10.1016/0301-0082(91)90036-Z contributor: fullname: Sivilotti L. – volume: 35 start-page: 455 year: 1996 ident: jo0507035b00021/jo0507035b00021_2 publication-title: Indian J. Chem. contributor: fullname: Osman A. N. – volume: 63 start-page: 2055 year: 1998 ident: jo0507035b00013/jo0507035b00013_2 publication-title: J. Org. Chem. doi: 10.1021/jo972141y contributor: fullname: Caron S. – volume: 124 start-page: 5287 year: 2002 ident: jo0507035b00007/jo0507035b00007_4 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja0259279 contributor: fullname: Okazawa T. – volume: 5 start-page: 4837 year: 2003 ident: jo0507035b00008/jo0507035b00008_1 publication-title: Org. Lett. contributor: fullname: Li W. – volume: 3 start-page: 1437 year: 2001 ident: jo0507035b00013/jo0507035b00013_1 publication-title: Org. Lett. doi: 10.1021/ol015598+ contributor: fullname: Kristensen J. – volume: 39 start-page: 8824 year: 1998 ident: jo0507035b00022/jo0507035b00022_1 publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(98)02043-7 contributor: fullname: Pfuller O. C. – volume: 6 start-page: 1162 year: 2004 ident: jo0507035b00029/jo0507035b00029_1 publication-title: Org. Lett. contributor: fullname: Park C.-H. – volume: 26 start-page: 940 year: 1999 ident: jo0507035b00003/jo0507035b00003_2 publication-title: Clin. Exp. Pharmacol. Physiol. doi: 10.1046/j.1440-1681.1999.03151.x contributor: fullname: Chebib M. – volume: 2 start-page: 3113 year: 2000 ident: jo0507035b00006/jo0507035b00006_2 publication-title: Org. Lett. doi: 10.1021/ol000183u contributor: fullname: Kondo Y. – volume: 125 start-page: 5275 year: 2003 ident: jo0507035b00006/jo0507035b00006_4 publication-title: J. Am. Chem. Soc. contributor: fullname: Sezen B. – volume: 41 start-page: 4211 year: 2002 ident: jo0507035b00030/jo0507035b00030_1 publication-title: Angew. Chem., Int. Ed. – volume: 1 start-page: 314 year: 1997 ident: jo0507035b00037/jo0507035b00037_1 publication-title: Org. Proc. Res. Dev. doi: 10.1021/op970107f contributor: fullname: Rosso V. W. – volume: 69 start-page: 569 year: 2004 ident: jo0507035b00014/jo0507035b00014_1 publication-title: J. Org. Chem. doi: 10.1021/jo035184p contributor: fullname: Szumigala R. H. – volume: 37 start-page: 6551 year: 1996 ident: jo0507035b00016/jo0507035b00016_1 publication-title: Tetrahedron Lett. doi: 10.1016/0040-4039(96)01398-6 contributor: fullname: Mongin F. – ident: jo0507035b00038/jo0507035b00038_1 doi: 10.1002/1615-9314(20020901)25:13<847::AID-JSSC847>3.0.CO;2-2 – volume: 3 start-page: 1557 year: 2001 ident: jo0507035b00035/jo0507035b00035_1 publication-title: Org. Lett. doi: 10.1021/ol015850d contributor: fullname: LeBlond C. R. – ident: jo0507035b00033/jo0507035b00033_1 – volume: 33 start-page: 272 year: 1992 ident: jo0507035b00006/jo0507035b00006_3 publication-title: Heterocycles contributor: fullname: Aoyagi Y. – volume: 121 start-page: 3540 year: 1999 ident: jo0507035b00010/jo0507035b00010_1 publication-title: J. Am. Chem. Soc. contributor: fullname: Kondo Y. – volume: 5 start-page: 2274 year: 2003 ident: jo0507035b00026/jo0507035b00026_1 publication-title: Org. Lett. doi: 10.1021/ol034602+ contributor: fullname: Limanto J. – volume: 6 start-page: 2900 year: 2004 ident: jo0507035b00007/jo0507035b00007_5 publication-title: Org. Lett. contributor: fullname: Lane B. S. – volume: 122 start-page: 4028 year: 2000 ident: jo0507035b00031/jo0507035b00031_1 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja0002058 contributor: fullname: Littke A. F. – volume: 21 start-page: 19 year: 2000 ident: jo0507035b00002/jo0507035b00002_1 publication-title: Trends Pharmacol. Sci. doi: 10.1016/S0165-6147(99)01413-3 contributor: fullname: Bormann J. – volume: 42 start-page: 2003008418 year: 2003 ident: jo0507035b00004/jo0507035b00004_1 publication-title: PCT Int. Appl. contributor: fullname: Carling W. R. – volume: 64 start-page: 3805 year: 1999 ident: jo0507035b00032/jo0507035b00032_2 publication-title: J. Org. Chem. contributor: fullname: Zhang C. – volume: 156 start-page: 2002038568 year: 2002 ident: jo0507035b00005/jo0507035b00005_1 publication-title: PCT Int. Appl. contributor: fullname: Bettati M. – volume: 3 start-page: 1680 year: 2001 ident: jo0507035b00007/jo0507035b00007_2 publication-title: Org. Lett. doi: 10.1021/ol0158866 contributor: fullname: McClure M. S. – volume: 12 start-page: 103 year: 1964 ident: jo0507035b00021/jo0507035b00021_1 publication-title: Chem. Pharm. Bull. contributor: fullname: Ueda T. – volume: 31 start-page: 1958 year: 1990 ident: jo0507035b00007/jo0507035b00007_1 publication-title: Heterocycles contributor: fullname: Ohta A. – volume-title: Metal catalyzed cross-coupling reactions year: 1998 ident: jo0507035b00009/jo0507035b00009_1 doi: 10.1002/9783527612222 contributor: fullname: Deiterich F. – volume: 59 start-page: 6394 year: 1994 ident: jo0507035b00036/jo0507035b00036_1 publication-title: J. Org. Chem. doi: 10.1021/jo00100a048 contributor: fullname: Larsen R. D. – volume: 125 start-page: 10585 year: 2003 ident: jo0507035b00006/jo0507035b00006_5 publication-title: J. Am. Chem. Soc. contributor: fullname: Sezen B. – volume: 5 start-page: 304 year: 2003 ident: jo0507035b00007/jo0507035b00007_3 publication-title: Org. Lett. doi: 10.1021/ol027266q contributor: fullname: Glover B. – volume: 7 start-page: 199 year: 2000 ident: jo0507035b00003/jo0507035b00003_3 publication-title: Curr. Med. Chem. doi: 10.2174/0929867003375380 contributor: fullname: Armer R. – volume: 31 start-page: 401 year: 1994 ident: jo0507035b00020/jo0507035b00020_1 publication-title: J. Heterocycl. Chem. doi: 10.1002/jhet.5570310226 – volume: 53 start-page: 831 year: 1988 ident: jo0507035b00025/jo0507035b00025_1 publication-title: J. Org. Chem. doi: 10.1021/jo00239a027 contributor: fullname: Ballistreri F. P. |
| SSID | ssj0000555 |
| Score | 1.8161864 |
| Snippet | A convergent, practical, and efficient synthesis of 2',6-difluoro-5'-[3-(1-hydroxy-1-methylethyl)imidazo[1,2-b][1,2,4]triazin-7-yl]biphenyl-2-carbonitrile (1),... |
| SourceID | proquest crossref pubmed |
| SourceType | Aggregation Database Index Database |
| StartPage | 5938 |
| SubjectTerms | Acetaldehyde - analogs & derivatives Acetaldehyde - chemistry Bromides - chemistry Catalysis GABA Agonists - chemical synthesis Hydrocarbons, Aromatic - chemistry Imidazoles - chemistry Palladium - chemistry Receptors, GABA-A Stereoisomerism Structure-Activity Relationship Triazines - chemical synthesis Triazoles - chemistry |
| Title | Palladium-catalyzed regioselective arylation of imidazo[1,2-b][1,2,4]triazine: synthesis of an alpha 2/3-selective GABA agonist |
| URI | https://www.ncbi.nlm.nih.gov/pubmed/16018689 https://search.proquest.com/docview/68035829 |
| Volume | 70 |
| hasFullText | 1 |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV3JTsMwELUqLnBhX8pqAce6TZzESbiFQilIIERBqoSqynYcVBAJos2hPSFx4nP4ET6CL2GcEBYhELco0jiRPZ554xm_QWhbgJYAqmAk9JkitvA48ZjPCfWVFQnlRIbSF4WPT1jzwj5qO-0S2volg0_N2nViOFovM55Sl-myvaDe-rS2juN8MIJTZhXsQV8lv_ucX4Bk5lAaU2ivuJaT15HcVNOBqMrRT5bGv_51Gk2-A0oc5Bowg0oqnkXj9aKP2xx6PNVn5WEvvSV1fVYzHKkQn6mrXtLPeuCAuQPpYV4Th5MIH972Qj5KLs0KJVjgjn6o2B3d30NTUe-8Pjzh1jAG5Njv9bUAj_HLM6Y1bGHS-hjzINgNcHCVaGreeXTR2D-vN8l76wUiwWH5YJldGcEGEgCPItdQOu6DF7amMXapw00JSMiNAGtEypKhaXLBQwFQEcJRIWxpLaCxOInVEsLcliFzbY20wGNKk3sGldx2hDIz1qcy2iwWp3uXM2x0s8w4hcikmM8y2iiWrQvTp5MaPFZJ2u8yz9CXff0yWsxX83MQiDU95vnL__nACprISFkNl1C6isYG96laA7gxEOuZvr0Bnj3Now |
| link.rule.ids | 314,780,784,2765,27924,27925 |
| linkProvider | American Chemical Society |
| 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=Palladium-Catalyzed+Regioselective+Arylation+of+Imidazo%5B1%2C2-+b+%5D%5B1%2C2%2C4%5Dtriazine%3A%E2%80%89+Synthesis+of+an+%CE%B1+2%2F+3+-Selective+GABA+Agonist&rft.jtitle=Journal+of+organic+chemistry&rft.au=Gauthier%2C+Donald+R.&rft.au=Limanto%2C+John&rft.au=Devine%2C+Paul+N.&rft.au=Desmond%2C+Richard+A.&rft.date=2005-07-22&rft.issn=0022-3263&rft.eissn=1520-6904&rft.volume=70&rft.issue=15&rft.spage=5938&rft.epage=5945&rft_id=info:doi/10.1021%2Fjo0507035&rft.externalDBID=n%2Fa&rft.externalDocID=10_1021_jo0507035 |
| 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 |