N-PHENYL-1-AZA-2-CYANO-1,3-BUTADIENES - AN INTRAMOLECULAR HETERO-DIELS-ALDER STRATEGY FOR THE CONSTRUCTION OF 1,4-BENZODIAZEPINES

Authors
GOULAOUICDUBOIS C ADAMS DR SISTI NJ FOWLER FW GRIERSON DS
Citation
C. Goulaouicdubois et al., N-PHENYL-1-AZA-2-CYANO-1,3-BUTADIENES - AN INTRAMOLECULAR HETERO-DIELS-ALDER STRATEGY FOR THE CONSTRUCTION OF 1,4-BENZODIAZEPINES, Tetrahedron letters, 39(24), 1998, pp. 4283-4286
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
24
Year of publication
1998
Pages
4283 - 4286
Database
ISI
SICI code
0040-4039(1998)39:24<4283:N-AIH>2.0.ZU;2-W
Abstract
A new approach to the construction of tricyclic 1,4-benzodiazepines ha s been developed, based upon the intramolecular Diels-Alder (IMDA) rea ction of 2-cyano-1-azadienes. This study revealed the difficulties inh erent to the direct transformation of imine-amide 2 to azadiene 3, but demonstrated the efficiency of the intramolecular [4 + 2] cycloadditi on of azadiene 13 as a means to access benzodiazepines 14a,b (3 : 2 mi xture; 74% combined yield). (C) 1998 Elsevier Science Ltd. All rights reserved.