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Reactions of some pyranylidene esters with amines
Author(s) -
Van Allan J. A.,
Reynolds G. A.
Publication year - 1971
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.5570080523
Subject(s) - chemistry , isopropylamine , potassium hydroxide , pyridine , primary (astronomy) , tryptamines , medicinal chemistry , derivative (finance) , organic chemistry , tryptamine , biochemistry , physics , astronomy , financial economics , economics
The reactions of 4‐(2,2‐dimethyl‐4,6‐dioxo‐1,3‐dioxan‐5‐ylidene)‐2,6‐diphenyl‐4 H ‐pyran ( 1 ) with primary amines gave the corresponding 1‐substituted 1,4‐dihydropyridine derivatives. The related benzo derivative of 1 (12) and primary amines gave 3‐substituted 3,4‐dihydro‐2‐phenyl‐5 H ‐[1]benzopyrano[3,4‐ c ] pyridine‐4,5‐dione derivatives. With secondary amines, 12 gave 2‐phenyl‐4H,5H‐pyrano[3,4‐ c ] [1]benzopyrane‐4,5‐dione, and with isopropylamine, N,N ‐dimethylhydra‐zine, and methanolic potassium hydroxide, 12 gave 4‐phenacylcoumarin. Some reaction intermediates were isolated which indicate probable reaction paths. The reactions with amines were extended to a naphtho derivative of 1 (19) and to a thia homolog of 12 (24).