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

doi:10.1016/S0040-4039(98)00756-4

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

School of Engineering & Physical Sciences

Research output: Contribution to journal › Article › peer-review

17 Citations (Scopus)

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 language	English
Pages (from-to)	4283-4286
Number of pages	4
Journal	Tetrahedron Letters
Volume	39
Issue number	24
DOIs	https://doi.org/10.1016/S0040-4039(98)00756-4
Publication status	Published - 11 Jun 1998

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title = "N-phenyl-1-aza-2-cyano-1,3-butadienes: An intramolecular hetero diels- alder strategy for the construction of 1,4-benzodiazepines",

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).",

author = "Catherine Goulaouic-Dubois and Adams, \{David R.\} and Sisti, \{Nicholas J.\} and Fowler, \{Frank W.\} and Grierson, \{David S.\}",

year = "1998",

month = jun,

day = "11",

doi = "10.1016/S0040-4039(98)00756-4",

language = "English",

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journal = "Tetrahedron Letters",

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T1 - N-phenyl-1-aza-2-cyano-1,3-butadienes

T2 - An intramolecular hetero diels- alder strategy for the construction of 1,4-benzodiazepines

AU - Goulaouic-Dubois, Catherine

AU - Adams, David R.

AU - Sisti, Nicholas J.

AU - Fowler, Frank W.

AU - Grierson, David S.

PY - 1998/6/11

Y1 - 1998/6/11

N2 - 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).

AB - 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).

UR - https://www.scopus.com/pages/publications/0032507926

U2 - 10.1016/S0040-4039(98)00756-4

DO - 10.1016/S0040-4039(98)00756-4

M3 - Article

SN - 0040-4039

VL - 39

SP - 4283

EP - 4286

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 24

ER -

N-phenyl-1-aza-2-cyano-1,3-butadienes: An intramolecular hetero diels- alder strategy for the construction of 1,4-benzodiazepines

Abstract

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