N-Alkoxy-N-chloroureas in the synthesis of 3,4-dihydro-1H-2,1-benzoxazine-1-carboxamide and 1-alkoxy-1,3-dihydrobenzimidazol-2-ones

The cyclization of N -chloro- N -(2-phenylethoxy)urea in the presence of silver trifluoroacetate leads to the formation of 3,4-dihydro-1 H -2,1-benzoxazine-1-carboxamide, while N -alkoxy- N '-aryl- N -chloro-ureas in the presence of sodium acetate form 1-alkoxy-1,3-dihydrobenzimidazol-2-ones. T...

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Bibliographic Details
Published inChemistry of heterocyclic compounds (New York, N.Y. 1965) Vol. 49; no. 8; pp. 1195 - 1206
Main Authors Shtamburg, V. G., Shishkin, O. V., Shtamburg, V. V., Zubatyuk, R. I., Mazepa, A. V., Kostyanovsky, R. G.
Format Journal Article
LanguageEnglish
Published Boston Springer US 01.11.2013
Springer Nature
Springer
Subjects
Chemistry
Chemistry and Materials Science
Chemistry, Organic
Nitrogen
Organic Chemistry
Pharmacy
Physical Sciences
Resveratrol
Science & Technology
Urea
1-alkoxy-1,3-dihydrobenzimidazol-2-ones
2,1-benz-oxazine-1-carboxamide
3,4-dihydro-1
alkoxy
nitrogen-containing heterocycles
chloroureas
cyclization
ELECTROPHILIC AROMATIC-SUBSTITUTION
N-alkoxy-N-chloroureas
3,4-dihydro-1H-2,1-benzoxazine-1-carboxamide
NITROGEN
ACYLNITRENIUM IONS
METHOXYAMIDES
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Summary:The cyclization of N -chloro- N -(2-phenylethoxy)urea in the presence of silver trifluoroacetate leads to the formation of 3,4-dihydro-1 H -2,1-benzoxazine-1-carboxamide, while N -alkoxy- N '-aryl- N -chloro-ureas in the presence of sodium acetate form 1-alkoxy-1,3-dihydrobenzimidazol-2-ones. The structures of 3,4-dihydro-1 H -2,1-benzoxazine-1-carboxamide and 1-methoxy-6-nitro-1,3-dihydrobenzimidazol-2-one were examined by X-ray structural analysis.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-013-1363-5