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Synthesis of substituted dihydroisocarbostyrils from 5‐hydroxyamides obtained from dilithio‐ N ‐substituted o ‐toluamides
Author(s) -
Mao ChungLing,
Burnish I. T.,
Hauser Charles R.
Publication year - 1969
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.5570060114
Subject(s) - chemistry , condensation , sulfuric acid , butyllithium , medicinal chemistry , organic chemistry , catalysis , physics , thermodynamics
δ‐Hydroxyamides, prepared by condensation of ketones or aldehydes at the 2‐methyl group of N substituted o ‐toluamides by means of n ‐butyllithium, were cyclodehydrated with sulfuric acid to form 2,3‐disubstituted and 2,3,3‐trisubstituted 3,4‐dihydroisocarbostyriIs. Also, δ‐hydroxyamides obtained from condensation of ketones at the 2‐benzyl group of N ‐methyl‐ o ‐benzylbenzamide, were cyclodehydrated to give 2,3,3,4‐tetrasubstituted 3,4‐dihydroisocarbo‐styrils. All of the products appeared to be new. This new method, which involves an unusual acid catalyzed cyclodehydration, is convenient and apparently quite general.