Acta Chimica Sinica ›› 1988, Vol. 46 ›› Issue (11): 1134-1138. Previous Articles     Next Articles

Original Articles

二氧化碳: 一种同时提供亲核中心保护和亲电中心活化的试剂 XI:2-取代四氢噻唑的新合成方法

KATRITZKY, A.R;范伟强   

  1. 美国佛罗里达州立大学化学系
  • 发布日期:1988-11-15

Carbon dioxide: A reagent for the simutaneous protection of nucleophilic centers and the activation of alternative locations to electrophilic attack XI:A new synthetic route to the 2-substituted thiazolidines

KATRITZKY, A.R;FAN WEIQIANG   

  • Published:1988-11-15

Thiazolidine is readily converted into 2-substituted derivatives I [R = D, Me, Et, Bu, hexyl, octyl, CH2Ph, CO2H, CPh2OH, CH(OH)C6H4Me-4] in a 1-pot lithiation procedure, with CO2 as both an N protection agent and as an intermediate carbanion-stabilizing group. The procedure has 4 stages: (1) protection of the NH group by lithiation and subsequent treatment with CO2 to form the Li carbamate; (2) lithiation by Me3CLi to form the carbanion; (3) introduction of a substituent by reaction with an electrophile; (4) acidic removal of the N protecting group. The yields of the products are mostly moderate.

Key words: THIAZOLE P, CARBON DIOXIDE, CONSERVATION, ACTIVATING AGENT, NUCLEOPHILIC REACTION, CHEMICAL REAGENT, ELECTROPHILIC REACTION

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