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Regioselective Reduction of 2‐(Arylideneamino)isoindole‐1,3‐diones − Synthesis of Alkaloid Analogues by N ‐Acylhydrazonium Ion Aromatic π‐Cyclization
Author(s) -
FogainNinkam Alain,
Daïch Adam,
Decroix Bernard,
Netchitaïlo Pierre
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300072
Subject(s) - chemistry , regioselectivity , isoindole , benzaldehyde , alkaloid , medicinal chemistry , lewis acids and bases , organic chemistry , stereochemistry , catalysis
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)