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Updated: May 22, 2026

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Synthesis and biological studies of triazolo-/thiadiazolo-benzoxazines
Vijay V Dabholkar1, Rahul P Gavande
1Organic Research Laboratory, Department of Chemistry, KC College, Churchgate, Mumbai-400 020, India. ahulforever@indiatimes.com
Abstract:
Diethyl bromomalonate (2) with an equimolar amount of 2-aminophenol (1) in the presence of sodium fluoride undergoes a cyclization reaction to form 2H,4H-2-ethoxycarbonyl-3,4-dihydro-3-oxo-1,4-benzoxazine (3). Furthermore, compound 3 undergoes a condensation reaction with hydrazine hydrate in the presence of methanol to yield 2H,4H-2-hydrazinocarbonyl-3,4-dihydro-3-oxo-1,4-benzoxazine (4), which on further reaction with aryl isothiocyanates gave 2H,4H-2-[ (4'-substituted)-phenylthiosemicarbazino]-carbonyl-3,4-dihydro-3-oxo-1,4-benzoxazine (5). Compound 5 on treatment with NaOH, cone. H2SO4 and diethylmalonate (6). afforded 2H,4H-2-[2'H-3'-thioxo-4'-substituted phenyl-1',2',4'-triazole-5-yl]- 3,4-dihydro-3-oxo-1,4benzoxazine (7). 2H,4H-2-[2'-amino-(substituted)-phenyl-1,3',4'-thiadiazol-5-yl]-3,4-dihydro-3-oxo-1,4-benzoxazine (8) and 2H,4H-2-[5'H-5'-dihydro-2'-thioxo-3'-phenyl-4',6'-dioxo-1,3-diazine]-aminocarbonyl-3,4-dihydro-3-oxo-1,4-benzoxazine (9), respectively. The synthesized compounds were investigated for their antibacterial activities against Gram positive as well as Gram negative bacteria with ampicillin trihydrate as standard drug. Structures have been elucidated on the basis of spectral and chemical analyses.
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