Synthesis of Dibenzo[f,h][1,2,4]triazolo[3,4-b]quinazolines via a Two-Step Route with Water as the Only By-Product

Pingping Xue; Zichao Du; Tao Wang; Zunting Zhang

doi:10.1055/s-0034-1380455

Synthesis, Table of Contents

Synthesis 2015; 47(21): 3385-3391
DOI: 10.1055/s-0034-1380455

paper

Synthesis of Dibenzo[f,h][1,2,4]triazolo[3,4-b]quinazolines via a Two-Step Route with Water as the Only By-Product

Authors

Pingping Xue

Key Laboratory of the Ministry of Education for Medicinal Resources and Natural Pharmaceutical Chemistry, National Engineering Laboratory for Resource Development of Endangered Crude Drugs in Northwest of China, and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an 710119, P. R. of China Email: zhangzunting@sina.com
Zichao Du

Key Laboratory of the Ministry of Education for Medicinal Resources and Natural Pharmaceutical Chemistry, National Engineering Laboratory for Resource Development of Endangered Crude Drugs in Northwest of China, and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an 710119, P. R. of China Email: zhangzunting@sina.com
Tao Wang

Key Laboratory of the Ministry of Education for Medicinal Resources and Natural Pharmaceutical Chemistry, National Engineering Laboratory for Resource Development of Endangered Crude Drugs in Northwest of China, and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an 710119, P. R. of China Email: zhangzunting@sina.com
Zunting Zhang*

Key Laboratory of the Ministry of Education for Medicinal Resources and Natural Pharmaceutical Chemistry, National Engineering Laboratory for Resource Development of Endangered Crude Drugs in Northwest of China, and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an 710119, P. R. of China Email: zhangzunting@sina.com

Abstract

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Abstract

Microwave-promoted cyclocondensation of isoflavones with 3-amino[1,2,4]triazole gave 6-phenyl-7-(2-hydroxyphenyl)-1,2,4triazolo[4,3-a]pyrimidines as intermediates. Subsequent photocyclization of these intermediates delivered dibenzo[f,h][1,2,4]triazolo[3,4-b]quinazolines as final products. Water was the only by-product in this two-step procedure. The products showed distinct fluorescence properties both in solution and in the solid state .

Key words

microwave - cyclocondensation - photocyclization - quinazoline - fluorescence

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References

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