Me3SiCl-catalyzed tandem thiocyanation/cyclization of tryptamine and tryptophol derivatives

Kun Liang; Ruirui Hua; Hongquan Yin; Fu Xue Chen

doi:10.1016/j.tetlet.2023.154534

Me₃SiCl-catalyzed tandem thiocyanation/cyclization of tryptamine and tryptophol derivatives

Kun Liang, Ruirui Hua, Hongquan Yin, Fu Xue Chen^*

^*此作品的通讯作者

化学与化工学院

Beijing Institute of Technology

科研成果: 期刊稿件 › 文章 › 同行评审

2 引用（Scopus）

摘要

An efficient metal-free tandem thiocyanation/cyclization of tryptamine and tryptophol derivatives has been developed by using Me₃SiCl as the Lewis acid catalyst and N-thiocyanatosaccharin as the electrophilic thiocyanating source under mild conditions. Thus, various C₃-SCN pyrroloindolines and furoindolines were diasteroselectively produced in high yields (up to 96%) within 30 min. The protocol was practical and tolerable for diverse functional groups.

源语言	英语
文章编号	154534
期刊	Tetrahedron Letters
卷	123
DOI	https://doi.org/10.1016/j.tetlet.2023.154534
出版状态	已出版 - 23 6月 2023

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title = "Me3SiCl-catalyzed tandem thiocyanation/cyclization of tryptamine and tryptophol derivatives",

abstract = "An efficient metal-free tandem thiocyanation/cyclization of tryptamine and tryptophol derivatives has been developed by using Me3SiCl as the Lewis acid catalyst and N-thiocyanatosaccharin as the electrophilic thiocyanating source under mild conditions. Thus, various C3-SCN pyrroloindolines and furoindolines were diasteroselectively produced in high yields (up to 96%) within 30 min. The protocol was practical and tolerable for diverse functional groups.",

keywords = "Cyclization, Dearomatization, Electrophilic thiocyanation, Furoindoline, Pyrroloindoline",

author = "Kun Liang and Ruirui Hua and Hongquan Yin and Chen, {Fu Xue}",

note = "Publisher Copyright: {\textcopyright} 2023 Elsevier Ltd",

year = "2023",

month = jun,

day = "23",

doi = "10.1016/j.tetlet.2023.154534",

language = "English",

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journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Me3SiCl-catalyzed tandem thiocyanation/cyclization of tryptamine and tryptophol derivatives

AU - Liang, Kun

AU - Hua, Ruirui

AU - Yin, Hongquan

AU - Chen, Fu Xue

PY - 2023/6/23

Y1 - 2023/6/23

N2 - An efficient metal-free tandem thiocyanation/cyclization of tryptamine and tryptophol derivatives has been developed by using Me3SiCl as the Lewis acid catalyst and N-thiocyanatosaccharin as the electrophilic thiocyanating source under mild conditions. Thus, various C3-SCN pyrroloindolines and furoindolines were diasteroselectively produced in high yields (up to 96%) within 30 min. The protocol was practical and tolerable for diverse functional groups.

AB - An efficient metal-free tandem thiocyanation/cyclization of tryptamine and tryptophol derivatives has been developed by using Me3SiCl as the Lewis acid catalyst and N-thiocyanatosaccharin as the electrophilic thiocyanating source under mild conditions. Thus, various C3-SCN pyrroloindolines and furoindolines were diasteroselectively produced in high yields (up to 96%) within 30 min. The protocol was practical and tolerable for diverse functional groups.

KW - Cyclization

KW - Dearomatization

KW - Electrophilic thiocyanation

KW - Furoindoline

KW - Pyrroloindoline

UR - http://www.scopus.com/inward/record.url?scp=85158827601&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2023.154534

DO - 10.1016/j.tetlet.2023.154534

M3 - Article

AN - SCOPUS:85158827601

SN - 0040-4039

VL - 123

JO - Tetrahedron Letters

JF - Tetrahedron Letters

M1 - 154534

ER -

Me3SiCl-catalyzed tandem thiocyanation/cyclization of tryptamine and tryptophol derivatives

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Me₃SiCl-catalyzed tandem thiocyanation/cyclization of tryptamine and tryptophol derivatives