O-protected N-(2-nitrophenylsulfonyl)hydroxylamines: Novel reagents for the synthesis of hydroxamates
Preparative methods for novel O-protected N-(2-nitrophenylsulfonyl)hydroxylamines (8a-e) are described. Their versatility as intermediates en route to polyhydroxamates is exemplified by the synthesis of a non-amide DFO analog 22.
Saved in:
Published in | Synthesis (Stuttgart) no. 7; pp. 1086 - 1092 |
---|---|
Main Authors | , , , , , , |
Format | Journal Article |
Language | English |
Published |
STUTTGART
Thieme Medical Publishers
01.06.2001
|
Subjects | |
Online Access | Get more information |
Cover
Loading…
Abstract | Preparative methods for novel O-protected N-(2-nitrophenylsulfonyl)hydroxylamines (8a-e) are described. Their versatility as intermediates en route to polyhydroxamates is exemplified by the synthesis of a non-amide DFO analog 22. |
---|---|
AbstractList | Preparative methods for novel O-protected N-(2-nitrophenylsulfonyl)hydroxylamines (8a-e) are described. Their versatility as intermediates en route to polyhydroxamates is exemplified by the synthesis of a non-amide DFO analog 22. |
Author | Rosik, LO Reddy, PA Slomczynska, U Schall, OF Wheatley Marshall, GR McClurg, JP |
Author_xml | – sequence: 1 givenname: PA surname: Reddy fullname: Reddy, PA – sequence: 2 givenname: OF surname: Schall fullname: Schall, OF – sequence: 3 surname: Wheatley fullname: Wheatley – sequence: 4 givenname: LO surname: Rosik fullname: Rosik, LO – sequence: 5 givenname: JP surname: McClurg fullname: McClurg, JP – sequence: 6 givenname: GR surname: Marshall fullname: Marshall, GR – sequence: 7 givenname: U surname: Slomczynska fullname: Slomczynska, U |
BookMark | eNqNj8tOwzAURL0oEm1hxwd4CUKGa-fhmB2KeElVu-m-cuxrEpTaVewC-XuCygewmTObM9IsyMwHj4RccbjjUBT3kQkAznhelHJG5gCZYrKq-DlZxPgBAFJkak5www5DSGgSWrpm14L5Lg3h0KIf-3jsXZh40452CN9jr_edx_hA1-ETezqgfkefInVhoKlFGkc_IXaRBkdPjt7rhPGCnDndR7z845Jsn5-29StbbV7e6scVM6KUiTnLZQUOeS5Ac3RgKp1po_KSW9kg8qxStskBrQNbNCgVlq4RU4IpQYklqU6zX9gEF02H3uDuMHR7PYy76TMvVaZk-dtU3SWduuDrcPRpUm__r4ofmx5ulQ |
CitedBy_id | crossref_primary_10_1016_j_bmc_2006_07_011 crossref_primary_10_1016_j_tetlet_2004_04_105 crossref_primary_10_1016_S0960_894X_03_00473_6 crossref_primary_10_1002_chin_200139100 crossref_primary_10_1002_bip_10471 crossref_primary_10_1016_j_tetlet_2008_05_098 crossref_primary_10_1021_acs_inorgchem_9b00878 crossref_primary_10_1021_acs_oprd_0c00069 crossref_primary_10_1021_acs_joc_3c02739 |
ContentType | Journal Article |
DBID | 1KM 1KN BLEPL DTL FMEHY |
DOI | 10.1055/s-2001-14567 |
DatabaseName | Index Chemicus Current Chemical Reactions Web of Science Core Collection Science Citation Index Expanded Web of Science - Science Citation Index Expanded - 2001 |
DatabaseTitle | Web of Science |
DatabaseTitleList | Web of Science |
Database_xml | – sequence: 1 dbid: 1KN name: Current Chemical Reactions url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/woscc/search-with-editions?editions=WOS.CCR sourceTypes: Enrichment Source Index Database |
DeliveryMethod | no_fulltext_linktorsrc |
Discipline | Chemistry |
EndPage | 1092 |
ExternalDocumentID | 000169397600019 |
GroupedDBID | --- -DZ -~X .-4 .HR 0R~ 123 186 1KM 1KN 1UC 3EH 4.4 53G 6TJ 85S 8WZ A6W AAMFZ ABJNI ABTAH ACGFS ACNCT ADRHT AEDKO AFFNX AFZED ALMA_UNASSIGNED_HOLDINGS BLEPL BXHMU CAG COF CS3 DTL E.- EJD EWXKU F5P GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED IY8 L7B MVM N9A O9- QTC RIG ROL RTC TN5 UQL WH7 XJT XOL YNT YR2 ZCG ZE2 ZKB ZY4 |
ID | FETCH-LOGICAL-c267t-fd1780fe1420a1ef0c8a3ac9461d7bee1389db40edf0d5be79e6fb29e60c6092 |
ISICitedReferencesCount | 13 |
ISICitedReferencesURI | https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000169397600019 |
ISSN | 0039-7881 |
IngestDate | Tue Sep 17 23:08:23 EDT 2024 Fri Oct 25 20:26:04 EDT 2024 |
IsPeerReviewed | true |
IsScholarly | true |
Issue | 7 |
Keywords | PEPTIDES ACIDS nosyl protecting group Mitsunobu reaction ESTERS SOLID-PHASE alkylation N-ALKYLATION INHIBITORS hydroxamate solid-phase synthesis SECONDARY-AMINES |
Language | English |
LinkModel | OpenURL |
LogoURL | https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg |
MergedId | FETCHMERGED-LOGICAL-c267t-fd1780fe1420a1ef0c8a3ac9461d7bee1389db40edf0d5be79e6fb29e60c6092 |
PageCount | 7 |
ParticipantIDs | webofscience_primary_000169397600019CitationCount webofscience_primary_000169397600019 |
PublicationCentury | 2000 |
PublicationDate | 2001-06-01 |
PublicationDateYYYYMMDD | 2001-06-01 |
PublicationDate_xml | – month: 06 year: 2001 text: 2001-06-01 day: 01 |
PublicationDecade | 2000 |
PublicationPlace | STUTTGART |
PublicationPlace_xml | – name: STUTTGART |
PublicationTitle | Synthesis (Stuttgart) |
PublicationTitleAbbrev | SYNTHESIS-STUTTGART |
PublicationYear | 2001 |
Publisher | Thieme Medical Publishers |
Publisher_xml | – name: Thieme Medical Publishers |
References | Reichwein, JF (WOS:000071994100045) 1998; 39 BERGERON, RJ (WOS:A1995QC16000021) 1995; 60 Bowman, WR (WOS:A1997YE89100014) 1997; 53 Olivieri, NF (WOS:A1997WG07300001) 1997; 89 RICH, DH (WOS:A1983QD46200005) 1983; 48 Wuts, PGM (WOS:000073699300002) 1998; 39 Wilson, MW (WOS:000078334900009) 1999; 55 Bhatt, U (WOS:A1997XA41900010) 1997; 38 Patel, DV (WOS:A1996VM04800010) 1996; 39 Miller, SC (WOS:A1997WL64600035) 1997; 119 BERGERON, RJ (WOS:A1992KD45800012) 1992; 35 ALTENBURGER, JM (WOS:A1992JK74300014) 1992; 33 BICKEL, H (WOS:A1960WH79000031) 1960; 43 DIONIS, JB (WOS:A1989AZ84400044) 1989; 54 Conway, TT (WOS:000083039600001) 1999; 42 Miller, SC (WOS:000072740300039) 1998; 120 GREENE TW (WOS:000169397600019.13) 1999 Slomczynska, Urszula (BCI:BCI200100077892) 2000; 23 SINGHA, AS (WOS:A1982PA73700031) 1982; 21 Fukuyama, T (WOS:A1997XR61900028) 1997; 38 BERGERON, RJ (WOS:A1991GQ61500006) 1991; 34 FUKUYAMA, T (WOS:A1995RU19300003) 1995; 36 Barlaam, B (WOS:000076338400013) 1998; 39 |
References_xml | – volume: 33 start-page: 5055 year: 1992 ident: WOS:A1992JK74300014 article-title: USEFUL HYDROXYLAMINE DERIVATIVES FOR THE SYNTHESIS OF HYDROXAMIC ACIDS publication-title: TETRAHEDRON LETTERS contributor: fullname: ALTENBURGER, JM – start-page: 17 year: 1999 ident: WOS:000169397600019.13 publication-title: PROTECTIVE GROUPS OR contributor: fullname: GREENE TW – volume: 42 start-page: 4016 year: 1999 ident: WOS:000083039600001 article-title: Diethylcarbamoylating/nitroxylating agents as dual action inhibitors of aldehyde dehydrogenase: A disulfiram-cyanamide merger publication-title: JOURNAL OF MEDICINAL CHEMISTRY contributor: fullname: Conway, TT – volume: 34 start-page: 3182 year: 1991 ident: WOS:A1991GQ61500006 article-title: SYNTHESIS AND BIOLOGICAL EVALUATION OF HYDROXAMATE-BASED IRON CHELATORS publication-title: JOURNAL OF MEDICINAL CHEMISTRY contributor: fullname: BERGERON, RJ – volume: 60 start-page: 109 year: 1995 ident: WOS:A1995QC16000021 article-title: A VERSATILE SYNTHESIS OF DEFERRIOXAMINE-B publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: BERGERON, RJ – volume: 39 start-page: 7865 year: 1998 ident: WOS:000076338400013 article-title: New hydroxylamines for the synthesis of hydroxamic acids publication-title: TETRAHEDRON LETTERS contributor: fullname: Barlaam, B – volume: 39 start-page: 1243 year: 1998 ident: WOS:000071994100045 article-title: Site-specific N-alkylation of peptides on the solid phase publication-title: TETRAHEDRON LETTERS contributor: fullname: Reichwein, JF – volume: 39 start-page: 4197 year: 1996 ident: WOS:A1996VM04800010 article-title: Hydroxamic acid-based bisubstrate analog inhibitors of Ras farnesyl protein transferase publication-title: JOURNAL OF MEDICINAL CHEMISTRY contributor: fullname: Patel, DV – volume: 39 start-page: 3889 year: 1998 ident: WOS:000073699300002 article-title: A cautionary note on the use of p-nitrobenzenesulfonamides as protecting groups publication-title: TETRAHEDRON LETTERS contributor: fullname: Wuts, PGM – volume: 21 start-page: 361 year: 1982 ident: WOS:A1982PA73700031 article-title: REACTIONS OF N-ACYL-O-ALKYLHYDROXYLAMINES .4. PREPARATION OF SOME N-ARYLSULPHONYL-O-ALKYLHYDROXYLAMINES publication-title: INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY contributor: fullname: SINGHA, AS – volume: 35 start-page: 4739 year: 1992 ident: WOS:A1992KD45800012 article-title: STRUCTURAL ALTERATIONS IN DESFERRIOXAMINE COMPATIBLE WITH IRON CLEARANCE IN ANIMALS publication-title: JOURNAL OF MEDICINAL CHEMISTRY contributor: fullname: BERGERON, RJ – volume: 23 start-page: 265 year: 2000 ident: BCI:BCI200100077892 article-title: Hydroxamate analog libraries and evaluation of their iron affinity publication-title: Transfusion Science contributor: fullname: Slomczynska, Urszula – volume: 89 start-page: 739 year: 1997 ident: WOS:A1997WG07300001 article-title: Iron-chelating therapy and the treatment of thalassemia publication-title: BLOOD contributor: fullname: Olivieri, NF – volume: 55 start-page: 1647 year: 1999 ident: WOS:000078334900009 article-title: A facile rearrangement of N-alkyl, N-(o or p-nitrophenylsulfonamide)-alpha-amino esters publication-title: TETRAHEDRON contributor: fullname: Wilson, MW – volume: 120 start-page: 2690 year: 1998 ident: WOS:000072740300039 article-title: oNBS-SPPS: A nem method for solid-phase peptide synthesis publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: Miller, SC – volume: 119 start-page: 2301 year: 1997 ident: WOS:A1997WL64600035 article-title: Site-selective N-methylation of peptides on solid support publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: Miller, SC – volume: 54 start-page: 5623 year: 1989 ident: WOS:A1989AZ84400044 article-title: SYNTHESIS AND ANALYTICAL CHARACTERIZATION OF A MAJOR DESFERRIOXAMINE-B METABOLITE publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: DIONIS, JB – volume: 36 start-page: 6373 year: 1995 ident: WOS:A1995RU19300003 article-title: 2-NITROBENZENESULFONAMIDES AND 4-NITROBENZENESULFONAMIDES - EXCEPTIONALLY VERSATILE MEANS FOR PREPARATION OF SECONDARY-AMINES AND PROTECTION OF AMINES publication-title: TETRAHEDRON LETTERS contributor: fullname: FUKUYAMA, T – volume: 48 start-page: 432 year: 1983 ident: WOS:A1983QD46200005 article-title: SYNTHESIS OF PROTECTED 2-AMINO-8-OXO-9,10-EPOXYDECANOIC ACID FROM 2-AMINOSUBERIC ACID-DERIVATIVES publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: RICH, DH – volume: 43 start-page: 2129 year: 1960 ident: WOS:A1960WH79000031 article-title: STOFFWECHSELPRODUKTE VON ACTINOMYCETEN .27. UBER DIE KONSTITUTION VON FERRIOXAMIN-B publication-title: HELVETICA CHIMICA ACTA contributor: fullname: BICKEL, H – volume: 38 start-page: 3679 year: 1997 ident: WOS:A1997XA41900010 article-title: Derivatized oxopiperazine rings from amino acids publication-title: TETRAHEDRON LETTERS contributor: fullname: Bhatt, U – volume: 53 start-page: 15787 year: 1997 ident: WOS:A1997YE89100014 article-title: A facile method for the N-alkylation of alpha-amino esters publication-title: TETRAHEDRON contributor: fullname: Bowman, WR – volume: 38 start-page: 5831 year: 1997 ident: WOS:A1997XR61900028 article-title: 2,4-dinitrobenzenesulfonamides: A simple and practical method for the preparation of a variety of secondary amines and diamines. publication-title: TETRAHEDRON LETTERS contributor: fullname: Fukuyama, T |
SSID | ssj0007239 |
Score | 1.7305734 |
Snippet | Preparative methods for novel O-protected N-(2-nitrophenylsulfonyl)hydroxylamines (8a-e) are described. Their versatility as intermediates en route to... |
Source | Web of Science |
SourceID | webofscience |
SourceType | Enrichment Source Index Database |
StartPage | 1086 |
SubjectTerms | Chemistry Chemistry, Organic Physical Sciences Science & Technology |
Title | O-protected N-(2-nitrophenylsulfonyl)hydroxylamines: Novel reagents for the synthesis of hydroxamates |
URI | http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000169397600019 |
WOS | 000169397600019 |
WOSCitedRecordID | wos000169397600019 |
hasFullText | |
inHoldings | 1 |
isFullTextHit | |
isPrint | |
link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV3LThsxFLUCXbQbRF8qhSIvWNCFqT2ZjDPsqgiEWpFIkErskJ8UCSaoGZCC-Hju9Tzi0CzSbpzImoxHc07sY98XIXuS29wLC3sTY6BJLGdKacmUTURqvJM-lAM6HWYnv9IfF72LTucpji4p9YF5XBpX8j-oQh_gilGy_4Bse1PogO-AL7SAMLQrYTxidZoFUI1DBloxYfAP_YOpAorZzfT-xqPfOWz2f88suqsA-ujljqcAw8mDw5T-6iqEuDXOhtNZAR91kpLqV-oW5WgsYs_bi2DI8_K-LK8URv60Zwpnztr4iC8YerBqC_aNjhcWgsawHIw-0-uqrPto4TAicpo6qMLZrt2ta21Mc8_-eAru5ujCKCJyyWgGxcpP0WoseFUq76-ZnvcwKcaUhacQIAPlfEVrrPgvFrrW_TAI3RyVWJC4a2RN9nF2FD9P21VcJt1q61Q_bh00AcN-iwddqleCNhlvko16U0G_Vwx5SzqueEdeD5pafu-Ji5hCh2x_KU--LrLkkAaO0IYjFDhCAXfacoROPI058oGMj4_GgxNWF9hgJslkybwVss-9E2nClXCem77qKpOnmbBSO4dGbKtT7qzntqedzF3mdQItNxkA85GsF5PCfSLUZ1ylmbFapybtWdPHcipdqRNptBfKb5G9-DVd3lWpVC5fILFFxCqXDer09Zi2ofy82q23yZs5YXfIKw9zgPsCgrLUuwH5Z-YqelU |
link.rule.ids | 786 |
linkProvider | Clarivate |
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=O-protected+N-%282-nitrophenylsulfonyl%29hydroxylamines%3A+Novel+reagents+for+the+synthesis+of+hydroxamates&rft.jtitle=Synthesis+%28Stuttgart%29&rft.au=Reddy%2C+PA&rft.au=Schall%2C+OF&rft.au=Wheatley&rft.au=Rosik%2C+LO&rft.date=2001-06-01&rft.pub=Thieme+Medical+Publishers&rft.issn=0039-7881&rft.issue=7&rft.spage=1086&rft.epage=1092&rft_id=info:doi/10.1055%2Fs-2001-14567&rft.externalDBID=n%2Fa&rft.externalDocID=000169397600019 |
thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0039-7881&client=summon |
thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0039-7881&client=summon |
thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0039-7881&client=summon |