Synthesis of [1,3,4]Thiadiazolo[3′,2′:1,2]imidazo[4,5-c]quinolines including Pictet–Spengler Reaction and Exploration of Their C-2 Reactivity through S_NAr

Abstract

This work reports the design of [1,3,4]thiadiazolo[3',2':1,2]imidazo[4,5-c]quinolines using a Pictet-Spengler reaction. The scope of the reaction was achieved from 6-(2-aminophenyl)imidazo[2,1-b][1,3,4]thiadiazole derivatives and available aldehydes. A wide range of aldehydes were employed to examine the scope of the cyclization. In parallel, a mechanism investigation was realized and showed a hydride transfer which led to a dismutation of the intermediate species. To complete this methodological study, a "sequential" oxidation/SAr procedure was performed to achieve C-2 nucleophilic substitution using several amine types.

A Facile One-Pot Synthesis of New Poly Functionalized Pyrrolotriazoles via a Regioselective Multicomponent Cyclisation and Suzuki–Miyaura Coupling Reactions

“…These conditions therefore appeared optimal for designing a representative library of compounds D. In order to introduce a wide range of functional groups, a solution consists in building a library of pyrrolo [2,3-d][1,2,3]triazole platforms D from commercially available 3pyrrholidinone C patterns and then elaborating its selective functionalization using arylation procedures. With this aim in view, our expertise in heterocyclic synthesis prompted us to envision the use of regioselective halogenation/Suzuki-Miyaura sequences from a versatile platform D that seems to be particularly powerful to tackle this challenge [28][29][30][31][32][33]. We report herein an unprecedented synthesis of tetra-substituted-pyrrolo [2,3d] [1,2,3]triazoles E, and the optimization of the experimental conditions.…”

Investigation of Ln3+ complexation by a DOTA derivative substituted by an imidazothiadiazole: synthesis, solution structure, luminescence and relaxation properties

“…[27][28][29][30][31][32][33][34][35][36] Therefore, imidazo[2,1-b] [1,3,4]thiadiazole and its derivatives have become important structures used in pharmaceutical chemistry. [37][38][39][40][41][42] The combination of coordinating properties and the biological potential of imidazothiazoles are appealing to generate original Ln 3+ complexes.…”

Synthesis of novel series of 3,5-disubstituted imidazo[1,2-d] [1,2,4]thiadiazoles involving SNAr and Suzuki–Miyaura cross-coupling reactions

“…For several years, our group has disclosed efficient methodologies to selectively functionalize bicyclic [5,5] heterocycles such as [1,2,4]triazolo[3,4- b ][1,3,4]thiadiazoles, 20 thiazolo[3,2- b ][1,2,4]triazoles 21 and more specially, imidazo[2,1- b ][1,3,4]thiadiazoles. 22–26 The latter have proven applicable to the discovery of a wide variety of biological molecules. Surprisingly, one of the isomers, the imidazo[1,2- d ][1,2,4]thiadiazole core, has seldom been described, and is reported in only a few references, where it has shown its potential as a therapeutic agent, especially as a Factor XIIIa inhibitor.…”