Synthesis of pyrimidine-6-carbonitriles, pyrimidin-5-ones, and tetrahydroquinoline-3-carbonitriles by new superb oxovanadium(V)-[5,10,15,20-tetrakis(pyridinium)-porphyrinato]-tetra(tricyanomethanide) catalyst via anomeric based oxidation

Mohammad Dashteh; Sajjad Makhdoomi; Saeed Baghery; Mohammad Ali Zolfigol; Ardeshir Khazaei; Yanlong Gu

doi:10.1038/s41598-022-23956-6

Synthesis of pyrimidine-6-carbonitriles, pyrimidin-5-ones, and tetrahydroquinoline-3-carbonitriles by new superb oxovanadium(V)-[5,10,15,20-tetrakis(pyridinium)-porphyrinato]-tetra(tricyanomethanide) catalyst via anomeric based oxidation

Sci Rep. 2022 Nov 14;12(1):19537. doi: 10.1038/s41598-022-23956-6.

Authors

Mohammad Dashteh¹, Sajjad Makhdoomi^{1

2}, Saeed Baghery³, Mohammad Ali Zolfigol⁴, Ardeshir Khazaei⁵, Yanlong Gu⁶

Affiliations

¹ Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, Hamedan, 6517838683, Iran.
² Department of Pharmacology and Toxicology, School of Pharmacy, Hamedan University of Medicinal Science, Hamedan, Iran.
³ Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, Hamedan, 6517838683, Iran. saadybaghery@yahoo.com.
⁴ Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, Hamedan, 6517838683, Iran. zolfi@basu.ac.ir.
⁵ Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, Hamedan, 6517838683, Iran. Khazaei_1326@yahoo.com.
⁶ School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, 1037 Luoyu Road, Hongshan District, Wuhan, 430074, People's Republic of China.

Abstract

Oxovanadium(V)-[5,10,15,20-tetrakis(pyridinium)-porphyrinato]-tetra(tricyanomethanide) [(VO)TPP][(TCM)₄] was designed, synthesized and characterized by various techniques such as FT-IR, EDX, SEM equipped with EDX mappings, CHN elemental analysis, ICP-OES, XRD, SEM, TEM, TGA, DTA, DRS, Kubelka-Munk function (Tauc's plot), and UV-Vis analyses. Then, [(VO)TPP][(TCM)₄] was used as a benign and expedient catalyst for the synthesis of numerous heterocyclic compounds such as 5-amino-7-(aryl)-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitriles, 5-amino-7-(aryl)-[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitriles, 7-(aryl)-7,12-dihydro-5H-isochromeno[4,3-d][1,2,4]triazolo[1,5-a]pyrimidin-5-ones, and 4-(aryl)-2-(1H-indol-3-yl)-5,6,7,8-tetrahydroquinoline-3-carbonitriles under solvent-free conditions at 100 °C via a cooperative geminal-vinylogous anomeric based oxidation.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Pyrimidines*
Quinolines*
Spectroscopy, Fourier Transform Infrared

Substances

1,2,3,4-tetrahydroquinoline
Pyrimidines
Quinolines