Premium
New synthesis and reactivity of 3‐bromoacetyl‐4‐hydroxy‐6‐methyl‐2 H ‐pyran‐2‐one with binucleophilic amines
Author(s) -
HikemOukacha Djamila,
Hamdi Maamar,
Silva Artur M. S.,
Yahia Rachedi
Publication year - 2011
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.507
Subject(s) - chemistry , pyran , dehydroacetic acid , pyridazine , bromine , acetic acid , stereochemistry , organic chemistry
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.