Microwave-Assisted Synthesis of s-Triazino[2,1-b][1,3]benzoxazoles, s-Triazino[2,1-b][1,3]benzothiazoles, and s-Triazino[1,2-a]benzimidazoles

Anton V. Dolzhenko; Wai-Keung Chui; Anna V. Dolzhenko

doi:10.1055/s-2006-926290

PAPER

Microwave-Assisted Synthesis of s-Triazino[2,1-b][1,3]benzoxazoles, s-Triazino[2,1-b][1,3]benzothiazoles, and s-Triazino[1,2-a]benzimidazoles [1]

Anton V. Dolzhenko^a, Wai-Keung Chui*^a, Anna V. Dolzhenko^b
^a Department of Pharmacy, Faculty of Science, National University of Singapore, 18 Science Drive 4, Singapore 117543, Singapore
^b Perm State Pharmaceutical Academy, 48 Lenin Street, Perm 614990, Russian Federation
Fax: +6567791554; e-Mail: phacwk@nus.edu.sg;

Abstract

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Abstract

2-Amino-4-oxo-derivatives of s-triazino[2,1-b][1,3]benzoxazoles, s-triazino[2,1-b][1,3]benzothiazoles, and s-triazino[1,2-a]benzimidazoles were synthesized by carbonylation of 2-benzoxazolylguanidines, 2-benzothiazolylguanidines, and 2-benzimidazolylguanidines with phenyl isocyanate under microwave irradiation (180 °C, 15 minutes). Using phenyl isothiocyanate instead of phenyl isocyanate under the same conditions led to the successful ring closure via thiocarbonylation of 2-benzoxazolylguanidines. However, the formation of 2-imino-4-phenylimino-s-triazino[2,1-b][1,3]benzothiazoles from 2-benzothiazolylguanidines was observed instead under microwave irradiation conditions.

Key words

carbonylation - microwave irradiation - triazinobenzoxazoles - triazinobenzothiazoles - triazinobenzimidazoles

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References

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