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Selective Synthesis of Benzothiophene‐Fused Polycyclic, Eight‐Membered N‐Heterocycles via Amine‐Mediated Three‐Component Domino Strategy
Author(s) -
Deng Qingsong,
Yu Aimin,
Zhang Lei,
Meng Xiangtai
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202001129
Subject(s) - benzothiophene , chemistry , tryptamine , cascade reaction , indole test , organic chemistry , domino , catalysis , stereochemistry , combinatorial chemistry , thiophene , biochemistry
A product‐selective strategy was used to synthesize benzothiophene‐fused polycyclic, eight‐membered N‐heterocycles via a three‐component domino reaction of thioisatins under catalyst‐free conditions. The reaction between tryptamine, thioisatin, and bromoacetophenone produced benzothiophene‐fused polycyclic compounds. In contrast, using D‐tryptophan methyl ester hydrochloride instead of tryptamine afforded benzothiophene‐fused eight‐membered N‐heterocycles. DFT calculations showed that the benzothiophene‐fused polycyclic compounds formed via the Pictet‐Spengler reaction. However, the ester group in D‐tryptophan methyl ester hydrochloride changed the reaction pathway and produced benzothiophene‐fused eight‐membered N‐heterocycles.