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Water‐Promoted Synthesis of Azepino[3,4,5‐ cd ]indole Analogues via Pictet‐Spengler Reaction
Author(s) -
Zhang Shuaizhong,
Cai Yunrui,
Zou Hongbin
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202000848
Subject(s) - indole test , pictet–spengler reaction , catalysis , combinatorial chemistry , substrate (aquarium) , chemistry , scope (computer science) , reaction conditions , biochemical engineering , organic chemistry , computer science , biology , ecology , engineering , programming language
Abstract Pictet‐Spengler reaction is an important strategy for the chemical or biosynthetic construction of alkaloids. Various suitable catalysts have thus been developed to drive the reaction. We herein report for the first time that water could directly catalyze the Pictet‐Spengler reactions of 2‐(1 H ‐indol‐4‐yl)ethanamines with aldehydes or ketones to generate azepino[3,4,5‐ cd ]indoles. Notably, this protocol is environmentally benign and highly practical with a wide substrate scope and promising gram‐scale applications. A plausible mechanism for this catalytic reaction is proposed to provide insights and potentially open a new avenue for organic synthesis.