Synthesis of ([1,2,4]triazolo[4,3- a ]pyridin-3-ylmethyl)phosphonates and their benzo derivatives via 5- exo - dig cyclization.

Autor: Krylov AS; Department of Organic Chemistry, Saint-Petersburg State Institute of Technology, Saint Petersburg, 190013, Russia., Petrosian AA; Department of Organic Chemistry, Saint-Petersburg State Institute of Technology, Saint Petersburg, 190013, Russia., Piterskaya JL; Department of Organic Chemistry, Saint-Petersburg State Institute of Technology, Saint Petersburg, 190013, Russia., Svintsitskaya NI; Department of Organic Chemistry, Saint-Petersburg State Institute of Technology, Saint Petersburg, 190013, Russia., Dogadina AV; Department of Organic Chemistry, Saint-Petersburg State Institute of Technology, Saint Petersburg, 190013, Russia.
Jazyk: angličtina
Zdroj: Beilstein journal of organic chemistry [Beilstein J Org Chem] 2019 Jul 12; Vol. 15, pp. 1563-1568. Date of Electronic Publication: 2019 Jul 12 (Print Publication: 2019).
DOI: 10.3762/bjoc.15.159
Abstrakt: A series of novel 3-methylphosphonylated [1,2,4]triazolo[4,3- a ]pyridines was accessed through a 5- exo - dig -type cyclization of chloroethynylphosphonates and commercially available N-unsubstituted 2-hydrazinylpyridines. In addition, 3-methylphosphonylated [1,2,4]triazolo[4,3- a ]quinolines and 1-methylphosphonylated [1,2,4]triazolo[3,4- a ]isoquinolines were synthesized in a similar manner. The presence of a NO 2 group in the starting hydrazinylpyridine induces a Dimroth-type rearrangement leading to 2-methylphosphonylated [1,2,4]triazolo[1,5- a ]pyridines.
Databáze: MEDLINE