A NEW APPROACH TO PYRIMIDINE-TYPE HETEROCYCLES BASED ON PETRENKO–KRITSCHENKO SYNTHESIS

Authors

  • Tung Hai To Graduate University of Sciences and Technology, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Hanoi University of Science and Technology of Hanoi, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Hanoi
  • Dang Buu Tran University of Science and Technology of Hanoi, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Hanoi Ho Chi Minh City University of Education, 280 An Duong Vuong, Ho Chi Minh City
  • Thang Chien Pham VNU University of Science, Vietnam National University, Hanoi, Department of Inorganic Chemistry, 19 Le Thanh Tong, Hanoi
  • Phong Dinh Tran University of Science and Technology of Hanoi, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Hanoi

DOI:

https://doi.org/10.1007/6884

Keywords:

multicomponent reaction, one-pot synthesis, Petrenko–Kritschenko reaction, pyrimidine synthesis, π–π stacking

Abstract

A new series of tetrahydropyrimidines were prepared by employing the Petrenko–Kritschenko reaction between 2-nitrobenzaldehyde and 1,3-dicarbonyl compounds in the presence of ammonium acetate at ambient temperature. The reaction afforded an unexpected heterocyclic skeleton instead of the usual piperidone ring. Physicochemical analyses including 1H, 13CNMR and HRMS were used to elucidate this structure. The stereochemistry was investigated by X-ray crystallography analysis and DFT calculations. The available results confirm the existence of an unusual structure containing two bulky groups at the cis position in the pyrimidine ring. Formation of such an exceptional structure is possible due to the π–π stacking stabilization of nitrophenyl groups.

Author Biography

Dang Buu Tran, University of Science and Technology of Hanoi, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Hanoi Ho Chi Minh City University of Education, 280 An Duong Vuong, Ho Chi Minh City

Department of Fundamental and Applied Science

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Published

2022-11-16

Issue

Vol. 58 No. 11 (2022)

Section

Original Papers