Investigation of N‐ and C‐Phosphanylation of [1,2,4]Triazolo[4,3‐<i>a</i>]pyridines

Marchenko, A. P.; Koidan, Heorgiy N.; Kyrylchuk, Andrii; Rozhenko, Alexander; Yurchenko, A. A.; Kostyuk, Alexander

doi:10.1002/hc.21258

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“…However, data on phosphorus-containing triazolopyridines are scarce, although the phosphoryl fragment widens the range of practical applications of such compounds. In this regard, Marchenko and co-workers [15] have reported the direct P(III)-phosphinylation of [1,2,4]triazolopyridines. The introduction of chlorethynylphosphonates in reactions with 2-hydrazinylpyridines allows to obtain methylphosphonylated triazolopyridine derivatives.…”

Section: Introductionmentioning

confidence: 99%

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

Krylov

Petrosian

Piterskaya

et al. 2019

Beilstein J. Org. Chem.

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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 NO2 group in the starting hydrazinylpyridine induces a Dimroth-type rearrangement leading to 2-methylphosphonylated [1,2,4]triazolo[1,5-a]pyridines.

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Section: Introductionmentioning

confidence: 99%