A New Method for the Synthesis of 3-Thiocyanatopyrazolo[1,5-a]pyrimidines

A New Method for the Synthesis of 3-Thiocyanatopyrazolo[1,5-a]pyrimidines Full article

Journal

Molecules
ISSN: 1420-3049

Output data

Year: 2020, Volume: 25, Number: 18, Article number : 4169, Pages count : DOI: 10.3390/molecules25184169

Authors

Kokorekin Vladimir A ^1,2,3 , Neverov Sergey V ³ , Kuzina Vera N ² , Petrosyan Vladimir A ³

Affiliations

1	All-Russian Research Institute of Phytopathology, Institute str. 5, Bol’shiye Vyazemy, 143050 Moscow, Russia
2	Institute of Pharmacy, Sechenov First Moscow State Medical University (Sechenov University), Trubetskaya str. 8, bldg. 2, 119991 Moscow, Russia
3	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp. 47, 119991 Moscow, Russia

In this article, we demonstrate how an original effective “metal-free” and “chromatography-free” route for the synthesis of 3-thiocyanatopyrazolo[1,5-a]pyrimidines has been developed. It is based on electrooxidative (anodic) C–H thiocyanation of 5-aminopyrazoles by thiocyanate ion leading to 4-thiocyanato-5-aminopyrazoles (stage 1, yields up to 87%) following by their chemical condensation with 1,3-dicarbonyl compounds or their derivatives (stage 2, yields up to 96%). This method is equally effective for the synthesis of 3-thiocyanatopyrazolo[1,5-a]pyrimidines, both without substituents and with various donor (acceptor) substituents in the pyrimidine ring.

Kokorekin V.A. , Neverov S.V. , Kuzina V.N. , Petrosyan V.A.
A New Method for the Synthesis of 3-Thiocyanatopyrazolo[1,5-a]pyrimidines
Molecules. 2020. V.25. N18. 4169 . DOI: 10.3390/molecules25184169 WOS Scopus OpenAlex

≡ Web of science:	WOS:000581974600001
≡ Scopus:	2-s2.0-85090847017
≡ OpenAlex:	W3084628787