SYNTHESIS OF 2-AMINO-4H-3,1-BENZOXAZINES AND 2-AMINO-4H-3,1-BENZOTHIAZINES BY THE REARRANGEMENT OF <i>o</i>-CYCLOPROPYLPHENYLUREAS AND <i>o</i>-CYCLOPROPYLPHENYLTHIOUREAS

Authors

  • А. Н. Федотов M. V. Lomonosov Moscow State University, Moscow 119992
  • Е. В. Трофимова M. V. Lomonosov Moscow State University, Moscow 119992
  • В. А. Романов M. V. Lomonosov Moscow State University, Moscow 119992
  • С. С. Мочалов M. V. Lomonosov Moscow State University, Moscow 119992
  • Ю. С. Шабаров M. V. Lomonosov Moscow State University, Moscow 119992
  • Н. С. Зефиров M. V. Lomonosov Moscow State University, Moscow 119992

DOI:

https://doi.org/10.1007/6944

Keywords:

2-arylamino-3, 1-benzoxazines, 1-benzothiazines, tautomers, N-(2-cyclo-propyl)phenylureas, N-(2-cyclopropyl)phenylthioureas, intramolecular rearrangements

Abstract

Syntheses are reported for 2-cyclopropylphenylureas and 2-cyclopropylphenylthioureas and the behavior of these compounds was studied under conditions for the acid-catalyzed opening of the cyclopropyl ring. Upon the action of concentrated sulfuric acid or trifluoroacetic acid, these ureas and thioureas can undergo rearrangement to the corresponding 3,1-benzoxazines and 3,1-benzothiazines.

How to Cite
Fedotov, A. N.; Trofimova, E. V.; Romanov, V. A.; Mochalov, S. S.;
Shabarov, Yu. S.; Zefirov, N. S.  Chem. Heterocycl. Compd. 2008, 44, 96. [Khim. Geterotsikl. Soedin. 2008, 115.]

For this article in the English edition see DOI 10.1007/s10593-008-0006-8


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Published

2022-08-04

Issue

No. 1 (2008)

Section

Original Papers