A MODIFIED BIGINELLI REACTION TOWARD OXYGEN-BRIDGED TETRAHYDROPYRIMIDINES FUSED WITH SUBSTITUTED 1,2,4-TRIAZOLE RING

Authors

  • Mustafa Kemal Gümüş Science-Technology Research and Application Center, Artvin Coruh University; SSI ''Institute for Single Crystals'' of National Academy of Sciences of Ukraine; V. N. Karazin Kharkiv National University
  • Nikolay Yu. Gorobets SSI ''Institute for Single Crystals'' of National Academy of Sciences of Ukraine
  • Yuriy V. Sedash SSI ''Institute for Single Crystals'' of National Academy of Sciences of Ukraine
  • Valentin A. Chebanov SSI ''Institute for Single Crystals'' of National Academy of Sciences of Ukraine; V. N. Karazin Kharkiv National University
  • Sergey M. Desenko SSI ''Institute for Single Crystals'' of National Academy of Sciences of Ukraine; V. N. Karazin Kharkiv National University

DOI:

https://doi.org/10.1007/4153

Keywords:

3-amino-1, 2, 4-triazole, benzoxadiazocine, oxygen-bridged structure, Biginelli reaction, cascade reaction, microwave-assisted synthesis, multicomponent reaction, reaction mechanism

Abstract

A microwave-assisted Biginelli-like three-component condensation using salicylic aldehyde derivatives, acetone, and 5-substituted 3-amino-1,2,4-triazoles instead of the urea component results in the formation of oxygen-bridged tetrahydrotriazolopyrimidine derivatives (11,12-dihydro-5,11-methano[1,2,4]triazolo[1,5-c][1,3,5]benzoxadiazocines) in good yields and high purity. A plausible reaction mechanism for this transformation is discussed in details using literature and experimental data.

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Published

2017-12-21

Issue

Vol. 53 No. 11 (2017)

Section

Original Papers