<i>N</i>-ALKOXY-<i>N</i>-CHLOROUREAS IN THE SYNTHESIS OF 3,4-DIHYDRO-1<i>H</i>-2,1-BENZOXAZINE-1-CARBOXAMIDE AND 1-ALKOXY-1,3-DIHYDROBENZIMIDAZOL-2-ONES

Authors

  • В. Г. Штамбург Ukrainian State University of Chemical Technologies
  • О. В. Шишкин State Scientific Institution "Institute for Single Crystals" of National Academy of Sciences of Ukraine
  • В. В. Штамбург National Technical University, Kharkiv Polytechnic Institute
  • Р. И. Зубатюк State Scientific Institution "Institute for Single Crystals" of National Academy of Sciences of Ukraine
  • А. В. Мазепа A. V. Bogatskii Physicochemical Institute, National Academy of Sciences of Ukraine
  • Р. Г. Костяновский N. N. Semenov Institute of Chemical Physics

DOI:

https://doi.org/10.1007/421

Keywords:

N-alkoxy-N-chloroureas, 1-alkoxy-1, 3-dihydrobenzimidazol-2-ones, 3, 4-dihydro-1H-2, 1-benzoxazine-1-carboxamide, nitrogen-containing heterocycles, cyclization

Abstract

The cyclization of N-chloro-N-(2-phenylethoxy)urea in the presence of silver trifluoroacetate leads to the formation of 3,4-dihydro-1H-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-1H-2,1-benzoxazine-1-carboxamide and 1-methoxy-6-nitro-1,3-dihydrobenzimidazol-2 one were examined by X-ray structural analysis.

Authors: V. G. Shtamburg, O. V. Shishkin, V. V. Shtamburg, R. I. Zubatyuk, A. V. Mazepa, and R. G. Kostyanovsky.

English Translation in Chemistry of Heterocyclic Compounds, 2013, 49 (8), pp 1195-1206

http://link.springer.com/article/10.1007/s10593-013-1363-5

Author Biographies

В. Г. Штамбург, Ukrainian State University of Chemical Technologies

Василий Георгиевич Штамбург

д.х.н, с.н.с., профессор кафедры органической химии Украинского государственного химико-технологического университета

О. В. Шишкин, State Scientific Institution "Institute for Single Crystals" of National Academy of Sciences of Ukraine

Олег Валерьевич Шишкин

д.х.н., профессор

В. В. Штамбург, National Technical University, Kharkiv Polytechnic Institute

Виктор Васильевич Штамбург

к.х.н., старший преподаватель кафедры органического синтеза и нанотехнологий

Р. И. Зубатюк, State Scientific Institution "Institute for Single Crystals" of National Academy of Sciences of Ukraine

Роман Иванович Зубатюк

к.х.н., с.н.с.

А. В. Мазепа, A. V. Bogatskii Physicochemical Institute, National Academy of Sciences of Ukraine

Александр Владимирович Мазепа

к.х.н, с.н.с.

Р. Г. Костяновский, N. N. Semenov Institute of Chemical Physics

Рэм Григорьевич Костяновский

д.х.н., профессор. зав. лаб. стереохимии

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Published

2013-06-17

Issue

No. 8 (2013)

Section

Original Papers