Chloroformate ester-induced reductive 1,2-bond cleavage of some 1,2,3,4-tetrahydro-β-carboline derivatives

Chloroformate ester-induced reductive 1,2-bond cleavage of some 1,2,3,4-tetrahydro-β-carboline derivatives
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氯甲酸酯诱导的一些 1,2,3,4-四氢-β-咔啉衍生物的 1,2-键还原断裂

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发表时间:
1982
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通讯作者:
M. Calverley
M. Calverley
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作者:
M. Calverley

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用氯甲酸酯在-70℃下处理,随后与NaBH3CN反应,1,2,5,6,11,11b-六氢- 3h -吲哚[3,2-g]吲哚嗪和1,2,3,4,6,7,12,12b-八氢吲哚[2,3-a]-喹诺嗪的衍生物干净地转化为相应的C/D环裂解脲烷衍生物;在0°C下进行的实验中,当试剂的添加顺序颠倒时,稳定底物-氰硼烷加合物的形成与该反应相竞争。
Treatment with a chloroformate ester at –70 °C and subsequent reaction with NaBH3CN converts 1,2,5,6,11,11b-hexahydro-3H-indolo[3,2-g]indolizine and derivatives of 1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]-quinolizine cleanly into the corresponding C/D ring-cleaved urethane derivatives; when the order of addition of reagents is reversed in experiments performed at 0 °C, formation of stable substrate–cyanoborane adducts competes with this reaction.