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^*

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

Beijing Institute of Technology

Research output: Contribution to journal › Article › peer-review

7 Citations (Scopus)

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.

Original language	English
Article number	154534
Journal	Tetrahedron Letters
Volume	123
DOIs	https://doi.org/10.1016/j.tetlet.2023.154534
Publication status	Published - 23 Jun 2023

Keywords

Cyclization
Dearomatization
Electrophilic thiocyanation
Furoindoline
Pyrroloindoline

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10.1016/j.tetlet.2023.154534

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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",

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

language = "English",

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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 - https://www.scopus.com/pages/publications/85158827601

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

Abstract

Keywords

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