Multicomponent Synthesis of 1,2,3-Triazol-4-yl-methylthio-3-arylquinazolin-4(3H)-one Derivatives

Multicomponent cyclization with azides to synthesize N-heterocycles

“…Like azides, alkynes can also be produced in situ by nucleophilic substitution reactions. Besides the classic S N 2 reaction, 34 alkynyl substrates are particularly accessible by Sonogashira alkynylation from (hetero)aryl or vinyl halides and terminal acetylenes in a concise fashion and under mild reaction conditions that are well-suited for elaboration into one-pot processes. 35 Consequently, this distinctive system has demonstrated its appropriateness for CuAAC, either sequentially or consecutively.…”

Multicomponent Syntheses based upon Copper‐Catalyzed Alkyne‐Azide Cycloaddition

“…[133] The propargylation approach also represents an entry to the combination of three bioactive entities, that is, the furanone ring, the 1,2,3-triazole ring and an amino acid, in the same molecule, thereby not only bringing out diversity but also potentially enhancing the bioacceptability of these conjugates. [135] Propargylic amides as alkynyl partners for CuAAC can be in principle obtained via acylation. [134] Thioureas are particularly nucleophilic in alkylations with alkyl halides.…”

“…Thioureas are particularly nucleophilic in alkylations with alkyl halides. A novel concomitant one‐pot synthesis of 1,2,3‐triazol‐4‐yl‐methylthio‐3‐arylquinazolin‐4(3 H )‐ones 64 ­ via propargylation of 2‐thioxo‐2,3‐dihydroquinazolin‐4(1 H )‐one followed by subsequent CuAAC has recently been reported (Scheme ) 135…”

A Sequentially Copper-Catalyzed Alkyne Carboxylation–Propargylation–Azide Cycloaddition (CuACPAC) Synthesis of 1,2,3-Triazolylmethyl Arylpropiolates

“…13 Propargylation of benzanellated thiopyrimidones also sets the stage for CuAAC in the consecutive three-component synthesis of 1,2,3-triazol-4-yl-methylthio-3arylquinazolin-4(3H)-ones. 14 In a similar fashion hydroxyl xanthen-11-one derivatives can be transformed by phenolate propargylation and subsequent CuAAC into a domino three-component reaction to give xanthene-triazole-quinoline conjugates. 15 Propargyl amides as transient interme-diates are formed in consecutive four-component syntheses of indole-3-glyoxyl-methyl 1,2,3-triazoles by glyoxylation of propargylamine, 16 or in a chemoenzymatic three-component synthesis of amide methyl-substituted 1,2,3-triazoles, 17 initiated by CAL-B-catalyzed aminolysis of methyl esters with propargylamine.…”