N-phenyl-1-aza-2-cyano-1,3-butadienes

An intramolecular hetero diels- alder strategy for the construction of 1,4-benzodiazepines

Catherine Goulaouic-Dubois, David R. Adams, Nicholas J. Sisti, Frank W. Fowler, David S. Grierson

Research output: Contribution to journalArticle

Abstract

A new approach to the construction of tricyclic 1,4-benzodiazepines has been developed, based upon the intramolecular Diels-Alder (IMDA) reaction of 2-cyano-1-azadienes. This study revealed the difficulties inherent to the direct transformation of imine-amide 2 to azadiene 3, but demonstrated the efficiency of the intramolecular [4 + 2] cycloaddition of azadiene 13 as a means to access benzodiazepines 14a,b (3 : 2 mixture; 74% combined yield).

Original languageEnglish
Pages (from-to)4283-4286
Number of pages4
JournalTetrahedron Letters
Volume39
Issue number24
DOIs
Publication statusPublished - 11 Jun 1998

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Imines
Cycloaddition
Benzodiazepines
Amides
Bz-423
1,3-butadiene

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Goulaouic-Dubois, Catherine ; Adams, David R. ; Sisti, Nicholas J. ; Fowler, Frank W. ; Grierson, David S. / N-phenyl-1-aza-2-cyano-1,3-butadienes : An intramolecular hetero diels- alder strategy for the construction of 1,4-benzodiazepines. In: Tetrahedron Letters. 1998 ; Vol. 39, No. 24. pp. 4283-4286.
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N-phenyl-1-aza-2-cyano-1,3-butadienes : An intramolecular hetero diels- alder strategy for the construction of 1,4-benzodiazepines. / Goulaouic-Dubois, Catherine; Adams, David R.; Sisti, Nicholas J.; Fowler, Frank W.; Grierson, David S.

In: Tetrahedron Letters, Vol. 39, No. 24, 11.06.1998, p. 4283-4286.

Research output: Contribution to journalArticle

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