Regioselective Reduction of 2‐(Arylideneamino)isoindole‐1,3‐diones − Synthesis of Alkaloid Analogues by N‐Acylhydrazonium Ion Aromatic π‐Cyclization
Identifieur interne : 000E44 ( France/Analysis ); précédent : 000E43; suivant : 000E45Regioselective Reduction of 2‐(Arylideneamino)isoindole‐1,3‐diones − Synthesis of Alkaloid Analogues by N‐Acylhydrazonium Ion Aromatic π‐Cyclization
Auteurs : Alain Fogain-Ninkam ; Adam Daïch ; Bernard Decroix [France] ; Pierre Netchitaïlo [France]Source :
- European Journal of Organic Chemistry [ 1434-193X ] ; 2003-11.
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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)
Url:
DOI: 10.1002/ejoc.200300072
Affiliations:
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ISTEX:6A018384956A55AEAE822799E4A059255DEFAED3Le document en format XML
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J. Org. 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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)</div></front></TEI><affiliations><list><country><li>France</li></country><region><li>Haute-Normandie</li><li>Région Normandie</li></region><settlement><li>Le Havre</li></settlement><orgName><li>Université du Havre</li></orgName></list><tree><noCountry><name sortKey="Daich, Adam" sort="Daich, Adam" uniqKey="Daich A" first="Adam" last="Daïch">Adam Daïch</name><name sortKey="Fogain Inkam, Alain" sort="Fogain Inkam, Alain" uniqKey="Fogain Inkam A" first="Alain" last="Fogain-Ninkam">Alain Fogain-Ninkam</name></noCountry><country name="France"><region name="Région Normandie"><name sortKey="Decroix, Bernard" sort="Decroix, Bernard" uniqKey="Decroix B" first="Bernard" last="Decroix">Bernard Decroix</name></region><name sortKey="Netchitailo, Pierre" sort="Netchitailo, Pierre" uniqKey="Netchitailo P" first="Pierre" last="Netchitaïlo">Pierre Netchitaïlo</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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