Carbonyl and thiocarbonyl compounds. XIX. Intramolecular cyclization of (2-nitroetheny1)aryl N-arylcarbamates : synthesis of newer series of 3,4-dihydro-2H-1,3-oxazin-2-ones and their antimicrobial activities

1982/05/01 by N Latif, N. LATIF, N Mishriky +2 · 1 citation
Biochemistry, Genetics and Molecular Biology · Chemistry · #Phenothiazines and Benzothiazines Synthesis and Activities #Synthesis and Biological Evaluation #Synthesis and Reactions of Organic Compounds

paper · doi:10.1071/ch9821037

openalex publication_date 1982/05/01 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/31

Abstract

The hitherto unknown 2-(2-nitroethenyl)aryl and 1-(2-nitroethenyl)naphthalen-2-yl N -arylcarbamates (2) and (5) are readily obtained through the uncatalysed interaction of aryl isocyanates with the corresponding 2-nitroethenyl phenols (1) and (4). The carbamates (2) and (5) cyclize readily at ambient temperature under base catalysis to the corresponding 3-aryl-4-nitromethyl-3,4-dihydro-2H-1,3-benzoxazin-2-ones (3) and 2-aryl-1-nitromethyl-2,3-dihydro-1H-naphth[l,2-e][1,3]oxazin-3-ones (6). The oxazinones (3) are cleaved by hot pyridine affording the corresponding 2-(2-nitroethenyl)phenols and N,N' -diarylurea, whereas, with butylamine, the corresponding aryl(butyl)urea and salicylaldehyde are obtained. The antimicrobial properties of the carbamates and benzoxazinones are evaluated.

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