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通过锂化-取代反应制备1-取代四氢-β-咔啉

Preparation of 1-Substituted Tetrahydro-β-carbolines by Lithiation-Substitution.

作者信息

Cochrane Edward J, Hassall Lorraine A, Coldham Iain

机构信息

†Department of Chemistry, University of Sheffield, Sheffield S3 7HF, United Kingdom.

‡AstraZeneca, Alderley Park, Macclesfield, Cheshire SK10 4TG, United Kingdom.

出版信息

J Org Chem. 2015 Jun 5;80(11):5964-9. doi: 10.1021/acs.joc.5b00725. Epub 2015 May 22.

Abstract

A method to prepare 1-substituted N-Boc-tetrahydro-β-carbolines was developed by lithiation followed by electrophilic substitution. The deprotonation to give the organolithium was optimized by in situ IR spectroscopy and showed that the Boc group rotates slowly at low temperature. The chemistry was applied to the synthesis of 9-methyleleagnine (N-methyltetrahydroharman) and 11-methylharmicine.

摘要

通过锂化反应随后进行亲电取代反应,开发了一种制备1-取代的N-叔丁氧羰基-四氢-β-咔啉的方法。通过原位红外光谱对去质子化生成有机锂的过程进行了优化,结果表明叔丁氧羰基在低温下旋转缓慢。该化学方法被应用于9-甲基胡颓子碱(N-甲基四氢哈尔满)和11-甲基哈尔明碱的合成。

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