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

Access to Document

10.1016/S0040-4039(98)00756-4

Cite this

@article{95008c32d29847afb231e8bd1ac40806,

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",

volume = "39",

pages = "4283--4286",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "24",

}

TY - JOUR

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 - http://www.scopus.com/inward/record.url?scp=0032507926&partnerID=8YFLogxK

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

Access to Document

Other files and links

Fingerprint

Cite this