Synthesis of 2,4-disubstituted thiazole combinatorial unit on solid-phase: microwave assisted conversion of alcohol to amine monitored by FT-IR

Abstract

Síntese em fase sólida com auxílio de radiação de microondas do tiazol 2,4-dissubstituído 3 com Resina Merrifield é descrita. As reações envolveram a conversão do grupo hidroxila em amina em cinco etapas-incluindo acoplamento e clivagem-com redimento total de 26% em duas horas de tempo reacional. Todas etapas da rota sintética foram eficientemente monitoradas por FT-IR em discos de KBr, demonstrando que esse método pode ser usado em química combinatória. Microwave-assisted solid-phase synthesis of the 2,4-disubstituted thiazole 3 on Merrifield Resin is described. The hydroxyl moiety was converted to amine in five steps-including coupling and cleavage-within a total reaction time of 2 hours and 26% overall yield. The entire solid-phase synthesis was efficiently monitored by FT-IR/KBr pellets and allows potential use in combinatorial chemistry.

Porous polymer particles—A comprehensive guide to synthesis, characterization, functionalization and applications

“…Infrared (IR) analysis is probably the most facile instrument based method to detect functional groups (such as -OH, -NH 2 , C=O, C=C, C≡C, -SH and -N 3 ) and monitor the evolution of reactions on particles [9,218,301]. IR spectrometers are abundant and analysis time is short.…”

A Novel and highly selective conversion of alcohols, thiols, and silyl ethers to azides using the 2,4,6-trichloro[1,3,5]triazine/n-Bu4NN3 system

“…[2][3][4] Aliphatic azides are usually prepared by nucleophilic substitution of the corresponding halides or sulfonates by azide ion. [5][6][7][8] Due to the advantageous and attractive strategy of the direct synthesis of azides from alcohols, some limited methods have been developed. Along this line, methods based on Mitsunobu conditions [7][8][9][10][11] are widely applied.…”

“…[5][6][7][8] Due to the advantageous and attractive strategy of the direct synthesis of azides from alcohols, some limited methods have been developed. Along this line, methods based on Mitsunobu conditions [7][8][9][10][11] are widely applied. These methods utilize reagents such as hydrazoic acid, diphenylphosphoryl azide, the bispyridine complex of zinc azide or the tetrabromocyclohexadienone/Ph 3 P system as the azide source/nucleophilic component.…”