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New Synthetic Method of Pyrrole and Pyrrolidinone

Author: LiuShuai
Tutor: DingMingWu
School: Central China Normal University
Course: Organic Chemistry
Keywords: ketenimine amidine palladium-catalyzed aerobic oxidative pyrrole pyrrolidinone
CLC: O626.13
Type: Master's thesis
Year: 2012
Downloads: 27
Quote: 0
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Abstract


Compounds containing nitrogen are the components of potent drugs and bioactive natural products, therefore considerable effort toward their synthesis has been developed. Ketenimines are excellent building blocks for the synthesis of differently nitrogen heterocycles in synthetic methodology. Palladium-catalyzed aerobic oxidative alkene amination is a powerful method to form C-N bond, which was applied recently in the synthesis of nitrogen-containing heterocycles.In this dissertation, we use readily available reported compounds as starting materials, after classical Wittig reaction to form amidine derivatives. The cyclization of amidine derivatives afford nitrogen-containing compounds. The spectral properties and the cyclization conditions were also studied.Two series of29unreported N-heterocyclic compounds were synthesized, which can be summarized as following:1. We use allyl carboethoxymethylenetriphenylphosphorane or allyl carbomethoxymethylenetriphenylphosphorane as the starting materials. By Wittig reaction, we obtained allyl ketenimines, and then by "one pot" strategy to form amidine derivatives. The turnover step is by palladium-catalyzed aerobic oxidative alkene amination, at last we synthesized20unreported compounds. We described herein the first successfully palladium-catalyzed aerobic oxidative intramolecular amination of terminal alkenes leading to densely substituted pyrrole derivatives.2. We use1,4-dicarboethoxyl ylide or1,4-dicarbomethoxyl ylide as the starting materials. By Wittig reaction, the active intermediate ketenimines were produced. After adding amines and strong base, we obtained9unreported pyrrolidinone derivatives by "one pot" strategy.

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CLC: > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Heterocyclic compounds > Five heterocycles containing a single different atoms > Azoles ( pyrrole) family
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