Simple Synthesis of Fused Thiazolo[4,5-b]pyridines through Successive SNAr Processes

Simple Synthesis of Fused Thiazolo[4,5-b]pyridines through Successive SNAr Processes Full article

Journal

Synlett
ISSN: 0936-5214 , E-ISSN: 1437-2096

Output data

Year: 2020, Volume: 32, Number: 03, Pages: 277-282 Pages count : 6 DOI: 10.1055/s-0040-1705960

Authors

Starosotnikov Alexey M. ¹ , Bastrakov Maxim A. ¹ , Kachala Vadim V. ¹ , Fedyanin Ivan V. ¹ , Klimova Tatyana A. ¹ , Ivanova Victoria V. ¹ , Dalinger Igor L. ¹

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry RAS

A convenient process is described for the synthesis of novel thiazolo[4,5-b]pyridines fused with triazole or pyrimidine rings. The base-promoted reactions of 2-chloro-3-nitropyridines with 1,3-(S,N)-binucleophiles (triazole-5-thiols, 4-oxopyrimidine-2-thiones) resulted in nucleophilic substitution of the chlorine atom and subsequent S–N-type Smiles rearrangement followed by nucleophilic substitution of the nitro group. Reactions with pyrimidine-2-thiones were carried out as one-pot processes while, in the case of triazole-5-thiols, isolation of intermediate substitution products was found to be preferable.

Starosotnikov A.M. , Bastrakov M.A. , Kachala V.V. , Fedyanin I.V. , Klimova T.A. , Ivanova V.V. , Dalinger I.L.
Simple Synthesis of Fused Thiazolo[4,5-b]pyridines through Successive SNAr Processes
Synlett. 2020. V.32. N03. P.277-282. DOI: 10.1055/s-0040-1705960 WOS Scopus OpenAlex

Web of science:	WOS:000583033200002
Scopus:	2-s2.0-85095876706
OpenAlex:	W3096026291

DB	Citing
OpenAlex	5
Scopus	5
Web of science	3