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Synthesis of 5 H ‐1,2,3‐triazolo[4,3‐ a ][2]benzazepines from the baylis‐hillman adducts of 2‐alkynylbenzaldehydes
Author(s) -
Ko Seung Ho,
Lee KeeJung
Publication year - 2004
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570410422
Subject(s) - benzazepines , chemistry , adduct , intramolecular force , cycloaddition , azide , nucleophilic substitution , nucleophile , stereochemistry , nucleophilic addition , acetylation , medicinal chemistry , organic chemistry , catalysis , biochemistry , gene
The facile synthesis of 5 H ‐1,2,3‐triazolo[4,3‐ a ][2]benzazepines 5a‐d by the intramolecular 1,3‐dipolar cycloaddition reaction of 2‐alkynylphenylallyl azides 4a‐d is described. The latter were readily obtained from 2‐alkynylbenzaldehydes 1a‐d through the Baylis‐Hillman adducts 2a‐d followed by acetylation to compounds 3a‐d and nucleophilic substitution by azide to compounds 4a‐d.