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A synthetic route to 1,4-disubstituted tetrahydro-β-carbolines and tetrahydropyranoindoles via ring-opening/Pictet–Spengler reaction of aziridines and epoxides with indoles/aldehydes†
Imtiyaz Ahmad Wani,Gaurav Goswami,Sahid Sk,Abhijit Mal,Masthanvali Sayyad,Manas K. Ghorai
Organic & Biomolecular Chemistry Pub Date : 12/04/2019 00:00:00 , DOI:10.1039/C9OB02098E
Abstract

A simple and efficient synthetic route to various 1,4-disubstituted tetrahydro-β-carbolines and tetrahydropyrano[3,4-b]indoles in high yields and stereoselectivity via LiClO4-catalyzed SN2-type ring opening of aziridines and epoxides with indoles followed by p-toluenesulfonic acid (PTSA) catalyzed Pictet–Spengler reaction is described.

Graphical abstract: A synthetic route to 1,4-disubstituted tetrahydro-β-carbolines and tetrahydropyranoindoles via ring-opening/Pictet–Spengler reaction of aziridines and epoxides with indoles/aldehydes
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