Intramolecular 1,3-dipolar cycloaddition as a route to triazolobenzodiazepines and pyrrolobenzodiazepines

Christopher S. Chambers, Nilesh Patel, Karl Hemming

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

Intramolecular 1,3-dipolar cycloaddition between an alkyne and an azide leads to a series of 1,2,3-triazolo-fused 1,4-benzodiazepines, 1,2,5-benzothiadiazepines, pyrrolobenzodiazepines and pyrrolobenzothiadiazepines (eight examples). The products are privileged structures in medicinal chemistry. The precursor azido alkynes are obtained, usually as transient intermediates, by treatment of the corresponding aldehydes (derived from α-amino acids) with the Bestmann-Ohira reagent.

LanguageEnglish
Pages4859-4861
Number of pages3
JournalTetrahedron Letters
Volume51
Issue number37
Early online date15 Jul 2010
DOIs
Publication statusPublished - 15 Sep 2010

Fingerprint

Alkynes
Cycloaddition
Cycloaddition Reaction
Pharmaceutical Chemistry
Aldehydes
Amino Acids
pyrrolo(2,1-c)(1,4)benzodiazepine
Bz-423
lead azide

Cite this

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Intramolecular 1,3-dipolar cycloaddition as a route to triazolobenzodiazepines and pyrrolobenzodiazepines. / Chambers, Christopher S.; Patel, Nilesh; Hemming, Karl.

In: Tetrahedron Letters, Vol. 51, No. 37, 15.09.2010, p. 4859-4861.

Research output: Contribution to journalArticle

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