Synthesis of N‐Bridged 6,8‐Dinitrotriazolo[1,5‐a]pyridines

Synthesis of N‐Bridged 6,8‐Dinitrotriazolo[1,5‐a]pyridines Full article

Journal

ChemistrySelect
ISSN: 2365-6549

Output data

Year: 2019, Volume: 4, Number: 4, Pages: 1510-1515 Pages count : 6 DOI: 10.1002/slct.201803068

Authors

Starosotnikov Alexey M. ¹ , Bastrakov Maxim A. ¹ , Knyazev Daniil A. ² , Fedyanin Ivan V. ³ , Kachala Vadim V. ¹ , Dalinger Igor L. ¹

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry RAS, Leninsky prosp. 47, Moscow, 119991 Russia
2	Higher Chemical College, D. Mendeleev University of Chemical Technology of Russia, Miusskaya sq. 9, Moscow, 125047 Russia
3	A.N. Nesmeyanov Institute of Organoelement Compounds RAS, Vavilova str. 28, Moscow, 119991 Russia

Facile and efficient protocols for the synthesis of 2-R-6,8-dinitro[1,2,4]triazolo[1,5-a]pyridines from commercially available starting materials have been developed. The reactions proceed via cyclization of corresponding 3,5-dinitropyridine-2-yl hydrazides or aldehyde 3,5-dinitropyridine-2-yl hydrazones followed by in situ Dimroth rearrangement to provide these triazole fused bicyclic heterocycles in good yields under mild conditions. Another synthetic route to target N-bridged dinitro[1,2,4]triazolo[1,5-a]pyridines includes arylation of 5-aryltetrazoles with 2-chloro-3,5-dinitropyridine and subsequent thermal decomposition/cyclization.

Starosotnikov A.M. , Bastrakov M.A. , Knyazev D.A. , Fedyanin I.V. , Kachala V.V. , Dalinger I.L.
Synthesis of N‐Bridged 6,8‐Dinitrotriazolo[1,5‐a]pyridines
ChemistrySelect. 2019. V.4. N4. P.1510-1515. DOI: 10.1002/slct.201803068 WOS Scopus OpenAlex

Web of science:	WOS:000457441400056
Scopus:	2-s2.0-85060889013
OpenAlex:	W2913947506

DB	Citing
OpenAlex	20
Scopus	21
Web of science	19