Continued Exploration of Trifunctional Alkyl 4-Chloro-2-diazo-3-oxobutanoates: Streamlined Entry into [1,2,3]Triazolo[5,1- c ][1,4]benzoxazines and [1,2,3]Triazolo[5,1- c ][1,4]benzoxazepines.

Autor: Budeev, Anton V., Kantin, Grigory, Dar'in, Dmitry, Krasavin, Mikhail
Předmět:
Zdroj: Synthesis; 2021, Vol. 53 Issue 12, p2155-2166, 12p
Abstrakt: Further exploration of the trifunctional character of previously introduced alkyl 4-chloro-2-diazo-3-oxobutanoates in reactions with N -protected substituted o -aminophenols followed by deprotection provided a convenient entry into [1,2,3]triazolo[5,1- c ][1,4]benzoxazines, which are of high medicinal importance, as documented in the literature. The same approach applied to N -protected substituted o -(aminomethyl)phenols afforded [1,2,3]triazolo[5,1- c ][1,4]benzoxazepines, which are practically unexplored compounds from a medicinal chemistry perspective. The syntheses start with SN 2-type alkylation of the phenol. Removal of the protecting group triggers imine formation followed by Wolff 1,2,3-triazole synthesis. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index