[3+3] Cyclocondensation of β-carbonyl-substituted 1H-benzo[f]chromenes with 3-amino-1,2,4-triazoles: synthesis of [1,2,4]triazolo[1,5-a]pyrimidines

The reaction of β-carbonyl-substituted 1 H -benzo[ f ]chromenes with 3-amino-1,2,4-triazoles provides a new avenue for the preparation of [1,2,4]triazolo[1,5- a ]pyrimidines containing a (2-hydroxynaphthalen-1-yl)methyl group at position 6. The reaction of 2-trifluoroacetyl-1 Н -benzo[ f ]chromene w...

Full description

Saved in:
Bibliographic Details
Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2022-11, Vol.58 (11), p.651-655
Main Authors: Osipov, Dmitry V., Korzhenko, Kirill S., Osyanin, Vitaly A., Krasnikov, Pavel E., Klimochkin, Yuri N.
Format: Article
Language:English
Subjects:
Carbonyls
Cascade chemical reactions
Chemistry
Chemistry and Materials Science
Michael reaction
Organic Chemistry
Pharmacy
Pyrimidines
Reaction mechanisms
Substitutes
Triazoles
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The reaction of β-carbonyl-substituted 1 H -benzo[ f ]chromenes with 3-amino-1,2,4-triazoles provides a new avenue for the preparation of [1,2,4]triazolo[1,5- a ]pyrimidines containing a (2-hydroxynaphthalen-1-yl)methyl group at position 6. The reaction of 2-trifluoroacetyl-1 Н -benzo[ f ]chromene with 3-amino-5-(methylsulfanyl)-1 H -1,2,4-triazole yielded a derivative of a new 4,5,5a,13a-tetrahydro-6 H -benzo-[5,6]chromeno[3,2- e ][1,2,4]triazolo[1,5- a ]pyrimidine heterocyclic system. The proposed cascade reaction mechanism includes an aza-Michael reaction, cyclodehydration, and a retro-oxa-Michael reaction.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-022-03129-z