Domino assembly of dithiocarbamatesviaCu-catalyzed denitrogenative thiolation of iodotriazole-based diazo precursors

Abstract

An efficient domino approach to assemble benzoxazoles and anthranilamides bearing dithiocarbamate moieties has been developed. The proposed route represents a Cu-catalyzed three-component reaction between readily available 5-iodo-1,2,3-triazoles, amines, and CS2....

Divergent cyclization of 2-(5-iodo-1,2,3-triazolyl)benzamides toward triazole-fused lactams and cyclic imidates

“…This route proved to be successful (Scheme 1A-7 and B) for the preparation of various triazole-fused sultams, 22 3,1-benzoxazines, 23 benzoxazinones, 24 and benzoxazoles. 25 We hypothesized that the reaction with ambident nucleophiles such as anions of secondary amides 1 can be controlled to provide both triazole-containing quinazolinones 2 and benzoxazine-imines 3 (Scheme 2). While there are several approaches for the preparation of 2 , ranging from classic condensation of azidobenzoic acid with electron deficient nitriles 26 to modern interrupted click 8 a and C–H activation, 11 these methods are somewhat limited in scope.…”

Regioselective Synthesis of NO-Donor (4-Nitro-1,2,3-triazolyl)furoxans via Eliminative Azide–Olefin Cycloaddition

“…In a series of nitrogen heterocycles, 1,2,3-triazoles have become of paramount importance over the past two decades due to their universal application in diverse fields, such as drug development and medicinal chemistry [37][38][39], materials science and polymers [40,41]. In addition, they contribute to organic synthesis by acting as synthetic precursors to many valuable compounds [42][43][44]. In this regard, nitro-1,2,3-triazoles acquire additional significance due to their potential application in energetic materials science and for medicinal chemistry needs [45][46][47].…”