Regioselective Reduction of 2-(Arylideneamino)isoindole-1,3-diones − Synthesis of Alkaloid Analogues by N-Acylhydrazonium Ion Aromatic π-Cyclization

Hydroxylactams 6a−c and 7a−c were synthesized by successive regioselective reductions of arylideneaminophthalimides 3a−c, which were easily available from aminophthalimide 1 and benzaldehyde (2a) or thiophenecarboxaldehydes 2b and 2c. N‐Acylhydrazonium ions III, generated in the presence of Lewis ac...

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	European journal of organic chemistry 2003-11, Vol.2003 (21), p.4273-4278
Hauptverfasser:	Fogain-Ninkam, Alain, Daïch, Adam, Decroix, Bernard, Netchitaïlo, Pierre
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkaloids Cyclization Nitrogen heterocycles Reduction
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

container_end_page	4278
container_issue	21
container_start_page	4273
container_title	European journal of organic chemistry
container_volume	2003
creator	Fogain-Ninkam, Alain Daïch, Adam Decroix, Bernard Netchitaïlo, Pierre
description	Hydroxylactams 6a−c and 7a−c were synthesized by successive regioselective reductions of arylideneaminophthalimides 3a−c, which were easily available from aminophthalimide 1 and benzaldehyde (2a) or thiophenecarboxaldehydes 2b and 2c. N‐Acylhydrazonium ions III, generated in the presence of Lewis acid from acetoxy derivatives 8a and 9a of hydroxylactams 6a and 7a, or in organic acid medium directly from hydroxylactams 6b and 6c, induced the expected isoindolo‐phthalazines 10a and 11a and thienopyridazino‐isoindolones 12b and 12c. On the other hand, hydroxylactams 7b and 7c under acidic conditions gave the unexpected N‐thienylmethyl‐substituted thienopyridazino‐isoindolones 13b and 13c. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
doi_str_mv	10.1002/ejoc.200300072
format	Article
fullrecord	<record><control><sourceid>istex_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1002_ejoc_200300072</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>ark_67375_WNG_89H4BG5Z_V</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3252-c7a6c8eac72f79edd1a001fdd11e38b6fa78399ce39253bf607fb37c5a208e433</originalsourceid><addsrcrecordid>eNqFkLtOwzAUhiMEEteV2SNIuPjSxPEYqlJACCTuYrFc5wQMboziFggTIzMLj8U78CS4KkJsTP8_fN850p8k65R0KCFsG-686TBCOCFEsLlkiRIpMckkmY-9y7uYSn61mCyHcBcRmWV0Kfk4gRvrAzgwY_sI6ATKSWy-Rr5CDG8UTetsCTXoka39pg3e1qV3gOkWx2XkIKCvt3d02tbjWwg2TL3C3WvnbYmKOubNJDLDFh3hwrTuti0b_eJrOxmh_fimaPxIj61Bn6-41xpnX_T0_WqyUGkXYO0nV5Lz3f5Zbw8fHg_2e8UhNpylDBuhM5ODNoJVQkJZUk0IrWJS4Pkwq7TIuZQGuGQpH1YZEdWQC5NqRnLocr6SdGZ3TeNDaKBSD40d6aZVlKjprGo6q_qdNQpyJjxZB-0_tOofHPf-unjm2jCG519XN_cqE1yk6vJooHK5190ZpNfqgn8DXUqPxA</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Regioselective Reduction of 2-(Arylideneamino)isoindole-1,3-diones − Synthesis of Alkaloid Analogues by N-Acylhydrazonium Ion Aromatic π-Cyclization</title><source>Wiley-Blackwell Full Collection</source><creator>Fogain-Ninkam, Alain ; Daïch, Adam ; Decroix, Bernard ; Netchitaïlo, Pierre</creator><creatorcontrib>Fogain-Ninkam, Alain ; Daïch, Adam ; Decroix, Bernard ; Netchitaïlo, Pierre</creatorcontrib><description>Hydroxylactams 6a−c and 7a−c were synthesized by successive regioselective reductions of arylideneaminophthalimides 3a−c, which were easily available from aminophthalimide 1 and benzaldehyde (2a) or thiophenecarboxaldehydes 2b and 2c. N‐Acylhydrazonium ions III, generated in the presence of Lewis acid from acetoxy derivatives 8a and 9a of hydroxylactams 6a and 7a, or in organic acid medium directly from hydroxylactams 6b and 6c, induced the expected isoindolo‐phthalazines 10a and 11a and thienopyridazino‐isoindolones 12b and 12c. On the other hand, hydroxylactams 7b and 7c under acidic conditions gave the unexpected N‐thienylmethyl‐substituted thienopyridazino‐isoindolones 13b and 13c. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.200300072</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Alkaloids ; Cyclization ; Nitrogen heterocycles ; Reduction</subject><ispartof>European journal of organic chemistry, 2003-11, Vol.2003 (21), p.4273-4278</ispartof><rights>Copyright © 2003 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3252-c7a6c8eac72f79edd1a001fdd11e38b6fa78399ce39253bf607fb37c5a208e433</citedby><cites>FETCH-LOGICAL-c3252-c7a6c8eac72f79edd1a001fdd11e38b6fa78399ce39253bf607fb37c5a208e433</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fejoc.200300072$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.200300072$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Fogain-Ninkam, Alain</creatorcontrib><creatorcontrib>Daïch, Adam</creatorcontrib><creatorcontrib>Decroix, Bernard</creatorcontrib><creatorcontrib>Netchitaïlo, Pierre</creatorcontrib><title>Regioselective Reduction of 2-(Arylideneamino)isoindole-1,3-diones − Synthesis of Alkaloid Analogues by N-Acylhydrazonium Ion Aromatic π-Cyclization</title><title>European journal of organic chemistry</title><addtitle>Eur. J. Org. Chem</addtitle><description>Hydroxylactams 6a−c and 7a−c were synthesized by successive regioselective reductions of arylideneaminophthalimides 3a−c, which were easily available from aminophthalimide 1 and benzaldehyde (2a) or thiophenecarboxaldehydes 2b and 2c. N‐Acylhydrazonium ions III, generated in the presence of Lewis acid from acetoxy derivatives 8a and 9a of hydroxylactams 6a and 7a, or in organic acid medium directly from hydroxylactams 6b and 6c, induced the expected isoindolo‐phthalazines 10a and 11a and thienopyridazino‐isoindolones 12b and 12c. On the other hand, hydroxylactams 7b and 7c under acidic conditions gave the unexpected N‐thienylmethyl‐substituted thienopyridazino‐isoindolones 13b and 13c. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)</description><subject>Alkaloids</subject><subject>Cyclization</subject><subject>Nitrogen heterocycles</subject><subject>Reduction</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><recordid>eNqFkLtOwzAUhiMEEteV2SNIuPjSxPEYqlJACCTuYrFc5wQMboziFggTIzMLj8U78CS4KkJsTP8_fN850p8k65R0KCFsG-686TBCOCFEsLlkiRIpMckkmY-9y7uYSn61mCyHcBcRmWV0Kfk4gRvrAzgwY_sI6ATKSWy-Rr5CDG8UTetsCTXoka39pg3e1qV3gOkWx2XkIKCvt3d02tbjWwg2TL3C3WvnbYmKOubNJDLDFh3hwrTuti0b_eJrOxmh_fimaPxIj61Bn6-41xpnX_T0_WqyUGkXYO0nV5Lz3f5Zbw8fHg_2e8UhNpylDBuhM5ODNoJVQkJZUk0IrWJS4Pkwq7TIuZQGuGQpH1YZEdWQC5NqRnLocr6SdGZ3TeNDaKBSD40d6aZVlKjprGo6q_qdNQpyJjxZB-0_tOofHPf-unjm2jCG519XN_cqE1yk6vJooHK5190ZpNfqgn8DXUqPxA</recordid><startdate>200311</startdate><enddate>200311</enddate><creator>Fogain-Ninkam, Alain</creator><creator>Daïch, Adam</creator><creator>Decroix, Bernard</creator><creator>Netchitaïlo, Pierre</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>200311</creationdate><title>Regioselective Reduction of 2-(Arylideneamino)isoindole-1,3-diones − Synthesis of Alkaloid Analogues by N-Acylhydrazonium Ion Aromatic π-Cyclization</title><author>Fogain-Ninkam, Alain ; Daïch, Adam ; Decroix, Bernard ; Netchitaïlo, Pierre</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3252-c7a6c8eac72f79edd1a001fdd11e38b6fa78399ce39253bf607fb37c5a208e433</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>Alkaloids</topic><topic>Cyclization</topic><topic>Nitrogen heterocycles</topic><topic>Reduction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Fogain-Ninkam, Alain</creatorcontrib><creatorcontrib>Daïch, Adam</creatorcontrib><creatorcontrib>Decroix, Bernard</creatorcontrib><creatorcontrib>Netchitaïlo, Pierre</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Fogain-Ninkam, Alain</au><au>Daïch, Adam</au><au>Decroix, Bernard</au><au>Netchitaïlo, Pierre</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Regioselective Reduction of 2-(Arylideneamino)isoindole-1,3-diones − Synthesis of Alkaloid Analogues by N-Acylhydrazonium Ion Aromatic π-Cyclization</atitle><jtitle>European journal of organic chemistry</jtitle><addtitle>Eur. J. Org. Chem</addtitle><date>2003-11</date><risdate>2003</risdate><volume>2003</volume><issue>21</issue><spage>4273</spage><epage>4278</epage><pages>4273-4278</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>Hydroxylactams 6a−c and 7a−c were synthesized by successive regioselective reductions of arylideneaminophthalimides 3a−c, which were easily available from aminophthalimide 1 and benzaldehyde (2a) or thiophenecarboxaldehydes 2b and 2c. N‐Acylhydrazonium ions III, generated in the presence of Lewis acid from acetoxy derivatives 8a and 9a of hydroxylactams 6a and 7a, or in organic acid medium directly from hydroxylactams 6b and 6c, induced the expected isoindolo‐phthalazines 10a and 11a and thienopyridazino‐isoindolones 12b and 12c. On the other hand, hydroxylactams 7b and 7c under acidic conditions gave the unexpected N‐thienylmethyl‐substituted thienopyridazino‐isoindolones 13b and 13c. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ejoc.200300072</doi><tpages>6</tpages></addata></record>
fulltext	fulltext
identifier	ISSN: 1434-193X
ispartof	European journal of organic chemistry, 2003-11, Vol.2003 (21), p.4273-4278
issn	1434-193X 1099-0690
language	eng
recordid	cdi_crossref_primary_10_1002_ejoc_200300072
source	Wiley-Blackwell Full Collection
subjects	Alkaloids Cyclization Nitrogen heterocycles Reduction
title	Regioselective Reduction of 2-(Arylideneamino)isoindole-1,3-diones − Synthesis of Alkaloid Analogues by N-Acylhydrazonium Ion Aromatic π-Cyclization
url	https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-01T10%3A37%3A00IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-istex_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Regioselective%20Reduction%20of%202-(Arylideneamino)isoindole-1,3-diones%20%E2%88%92%20Synthesis%20of%20Alkaloid%20Analogues%20by%20N-Acylhydrazonium%20Ion%20Aromatic%20%CF%80-Cyclization&rft.jtitle=European%20journal%20of%20organic%20chemistry&rft.au=Fogain-Ninkam,%20Alain&rft.date=2003-11&rft.volume=2003&rft.issue=21&rft.spage=4273&rft.epage=4278&rft.pages=4273-4278&rft.issn=1434-193X&rft.eissn=1099-0690&rft_id=info:doi/10.1002/ejoc.200300072&rft_dat=%3Cistex_cross%3Eark_67375_WNG_89H4BG5Z_V%3C/istex_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true