Síntese de 1,2,3-triazóis contendo quinolinas e sulfonas via cicloadições catalisadas por pirrolidina

Abstract

This work presents the synthesis of new 1,2,3-triazole compounds using pyrrolidine as an organocatalyst in the 1,3-dipolar cycloadditions. First it was made the synthesis of 7-chloroquinoline-1H-1,2,3-triazoilcarboxylates 4a-l it from 4-azido-7-chloroquinoline 1 with various β-keto esters 2a-l, using pyrrolidine (10 mol%) as catalyst in dimethyl sulfoxide (DMSO) as solvent at room temperature, without an inert atmosphere and reaction time of 24 hours for the formation of the 7-chloroquinoline-1H-1,2,3-triazoil-carboxylates 4al, obtaining a variety of products good to excellent yields ranging from 41 to 98%. In a second study, the synthesis of organic azides 5a-j and β-keto sulfones 6a-l was performed to obtain 4-(arylsulfonyl)-1H-1,2,3-triazoles 1,5-disubstituted 7av. It was used pyrrolidine (5 mol%) as catalyst in dimethyl sulfoxide (DMSO) solvent at room temperature without the need for an inert atmosphere and reaction time of 24 hours. These reactions were efficient substrates for a variety of providing the desired products 7a-v, good to excellent yields under mild reaction conditions. The methodologies described, using the organocatalysis proven to be efficient for the synthesis of a series of 1,2,3-triazole in good yields and reaction times of 24 hours for various substrates.