Krylov Aleksandr S, Petrosian Artem A, Piterskaya Julia L, Svintsitskaya Nataly I, Dogadina Albina V
Department of Organic Chemistry, Saint-Petersburg State Institute of Technology, Saint Petersburg, 190013, Russia.
Beilstein J Org Chem. 2019 Jul 12;15:1563-1568. doi: 10.3762/bjoc.15.159. eCollection 2019.
A series of novel 3-methylphosphonylated [1,2,4]triazolo[4,3-]pyridines was accessed through a 5---type cyclization of chloroethynylphosphonates and commercially available N-unsubstituted 2-hydrazinylpyridines. In addition, 3-methylphosphonylated [1,2,4]triazolo[4,3-]quinolines and 1-methylphosphonylated [1,2,4]triazolo[3,4-]isoquinolines were synthesized in a similar manner. The presence of a NO group in the starting hydrazinylpyridine induces a Dimroth-type rearrangement leading to 2-methylphosphonylated [1,2,4]triazolo[1,5-]pyridines.
通过氯乙炔基膦酸酯与市售的 N-未取代 2-肼基吡啶的 5-型环化反应，得到了一系列新型的 3-甲基膦酰化[1,2,4]三唑并[4,3-]吡啶。此外，以类似方式合成了 3-甲基膦酰化[1,2,4]三唑并[4,3-]喹啉和 1-甲基膦酰化[1,2,4]三唑并[3,4-]异喹啉。起始肼基吡啶中 NO 基团的存在会引发迪姆罗思型重排，生成 2-甲基膦酰化[1,2,4]三唑并[1,5-]吡啶。
