苯甲酰叠氮作为高效中间体：吡咯烷和咪唑的一锅法合成

Phenacyl azides as efficient intermediates: one-pot synthesis of pyrrolidines and imidazoles.

作者信息

Reddy Chada Narsimha, Sathish Manda, Adhikary Susanta, Nanubolu Jagadeesh Babu, Alarifi Abdullah, Maurya Ram Awatar, Kamal Ahmed

机构信息

Department of Medicinal Chemistry and Biotechnology, CSIR-Indian Institute of Chemical Technology, Hyderabad-500007, India.

Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Hyderabad 500 037, India.

出版信息

Org Biomol Chem. 2017 Mar 28;15(13):2730-2733. doi: 10.1039/c7ob00299h.

DOI:10.1039/c7ob00299h

PMID:28304056

Abstract

Phenacyl azides were decomposed in basic media to generate N-unsubstituted imines which were reacted with cyclic amino acids to give an azomethine ylide that underwent [3 + 2] cycloaddition with maleimides and N-unsubstituted imines to yield various diastereoselective pyrrolidines and imidazoles respectively in a one-pot three component manner with good to excellent yields.

摘要

苯甲酰叠氮在碱性介质中分解生成N-未取代的亚胺，该亚胺与环状氨基酸反应生成甲亚胺叶立德，甲亚胺叶立德与马来酰亚胺和N-未取代的亚胺进行[3 + 2]环加成反应，分别以一锅三组分的方式以良好至优异的产率得到各种非对映选择性的吡咯烷和咪唑。