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New synthesis and reactivity of 3-bromoacetyl-4-hydroxy-6-methyl-2H-pyran-2-one with binucleophilic amines

✍ Scribed by Djamila Hikem-Oukacha; Maamar Hamdi; Artur M. S. Silva; Rachedi Yahia

Publisher
Journal of Heterocyclic Chemistry
Year
2010
Tongue
English
Weight
137 KB
Volume
48
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

3‐(Bromoacetyl)‐4‐hydroxy‐6‐methyl‐2__H__‐pyran‐2‐one was synthesized by the reaction of dehydroacetic acid (DHAA) with bromine in glacial acetic acid. Novel heterocyclic products were synthesized from the reaction of bromo‐DHAA with alkanediamines, phenylhydrazines, ortho‐phenylenediamines, and ortho‐aminobenzenethiol. The obtained new products 3‐(2‐N‐substituted‐acetyl)‐4‐hydroxy‐6‐methyl‐2__H__‐pyran‐2‐ones, 4‐hydroxy‐3‐[1‐hydroxy‐2‐(2‐phenylhydrazinyl)vinyl]‐6‐methyl‐2__H__‐pyran‐2‐one, 1‐(2,4‐dinitrophenyl)‐7‐methyl‐2,3‐dihydro‐1__H__‐pyrano[4,3‐c]pyridazine‐4,5‐dione, 3‐(3,4‐dihydroquinoxalin‐2‐yl)‐4‐hydroxy‐6‐methyl‐2__H__‐pyran‐2‐one/3‐(3,4‐dihydroquinoxalin‐2‐yl)‐6‐methyl‐2__H__‐pyran‐2,4(3__H__)‐dione, 6‐methyl‐3‐(3,4‐dihydroquinoxalin‐2‐yl)‐2__H__‐pyran‐2,4(3__H__)‐dione, and (E)‐3‐(2__H__‐benzo[b][1,4]thiazin‐3(4__H__)‐ylidene)‐6‐methyl‐2__H__‐pyran‐2,4(3__H__)‐dione were fully characterized by IR, ^1^H and ^13^C NMR, and mass spectra. J. Heterocyclic Chem., 2011.

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