Open Access Open Access  Restricted Access Subscription Access

REARRANGEMENT OF THIAZOLO[3,2-a]PYRIMIDINES INTO TRIAZOLO[4,3-a]PYRIMIDINES INDUCED BY C=N BOND REDUCTION

Eugenia A. Lashmanova, Artem S. Agarkov, Victor B. Rybakov, Andrey K. Shiryaev
Cover Image

Abstract


Triazolo[4,3-a]pyrimidines were prepared by the reduction of 5,6,7-trisubstituted 2-(arylhydrazinylidene)-5H-[1,3]thiazolo[3,2-a]pyrimidin-3(2H)-ones with NaBH4 in the presence of V2O5 at room temperature. The structure of ethyl 3-(hydroxymethyl)-5-(4-methoxyphenyl)-7-methyl-1-phenyl-1,5-dihydro[1,2,4]triazolo[4,3-a]pyrimidine-6-carboxylate was proven by the single crystal X-ray diffraction data. The mechanism of the reaction including transition cage structure is discussed.

Keywords


hydrazine derivatives; 2-hydrazinylidene-5H-[1,3]thiazolo[3,2-a]pyrimidin-3(2H)-one; [1,3]thiazolo[3,2-a]pyrimidine; [1,2,4]triazolo[4,3-a]pyrimidine; rearrangement; reduction; transition cage structure.

Full Text: PDF Supplementary File(s): supplementary info (13MB)


 

 

Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia - hgs@osi.lv