Friedel-Crafts cyclization of 2-(3-indolythio)propionic acids. An unusual rearrangement leading to 4-sulfur-substituted tricyclic indoles

John Y.L. Chung; Robert A. Reamer; Paul J. Reider

doi:10.1016/S0040-4039(00)61267-4

Friedel-Crafts cyclization of 2-(3-indolythio)propionic acids. An unusual rearrangement leading to 4-sulfur-substituted tricyclic indoles

John Y.L. Chung
, Robert A. Reamer
, Paul J. Reider

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

8 Scopus citations

Abstract

The intramolecular Friedel-Crafts acylation of 2-(3-indolythio)propionic acid 1 has been found to undergo an unprecedented rearrangement to provide a novel tricyclic indole having the sulfur substituted on C-4 rather than on the expected C-3. A mechanism for its formation is proposed. This rearrangement also proceeded with good optical retention when a chiral substrate was used.

Original language	English (US)
Pages (from-to)	4717-4720
Number of pages	4
Journal	Tetrahedron Letters
Volume	33
Issue number	33
DOIs	https://doi.org/10.1016/S0040-4039(00)61267-4
State	Published - Aug 11 1992
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

Keywords

4-thio-indoles
Friedel-Crafts acylation
rearrangement
thiopyrano-[4,3.2-c,d]indoles
tricyclic-indoles

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10.1016/S0040-4039(00)61267-4

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title = "Friedel-Crafts cyclization of 2-(3-indolythio)propionic acids. An unusual rearrangement leading to 4-sulfur-substituted tricyclic indoles",

abstract = "The intramolecular Friedel-Crafts acylation of 2-(3-indolythio)propionic acid 1 has been found to undergo an unprecedented rearrangement to provide a novel tricyclic indole having the sulfur substituted on C-4 rather than on the expected C-3. A mechanism for its formation is proposed. This rearrangement also proceeded with good optical retention when a chiral substrate was used.",

keywords = "4-thio-indoles, Friedel-Crafts acylation, rearrangement, thiopyrano-[4,3.2-c,d]indoles, tricyclic-indoles",

author = "Chung, \{John Y.L.\} and Reamer, \{Robert A.\} and Reider, \{Paul J.\}",

year = "1992",

month = aug,

day = "11",

doi = "10.1016/S0040-4039(00)61267-4",

language = "English (US)",

volume = "33",

pages = "4717--4720",

journal = "Tetrahedron Letters",

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publisher = "Elsevier Ltd",

number = "33",

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T1 - Friedel-Crafts cyclization of 2-(3-indolythio)propionic acids. An unusual rearrangement leading to 4-sulfur-substituted tricyclic indoles

AU - Chung, John Y.L.

AU - Reamer, Robert A.

AU - Reider, Paul J.

PY - 1992/8/11

Y1 - 1992/8/11

N2 - The intramolecular Friedel-Crafts acylation of 2-(3-indolythio)propionic acid 1 has been found to undergo an unprecedented rearrangement to provide a novel tricyclic indole having the sulfur substituted on C-4 rather than on the expected C-3. A mechanism for its formation is proposed. This rearrangement also proceeded with good optical retention when a chiral substrate was used.

AB - The intramolecular Friedel-Crafts acylation of 2-(3-indolythio)propionic acid 1 has been found to undergo an unprecedented rearrangement to provide a novel tricyclic indole having the sulfur substituted on C-4 rather than on the expected C-3. A mechanism for its formation is proposed. This rearrangement also proceeded with good optical retention when a chiral substrate was used.

KW - 4-thio-indoles

KW - Friedel-Crafts acylation

KW - rearrangement

KW - thiopyrano-[4,3.2-c,d]indoles

KW - tricyclic-indoles

UR - https://www.scopus.com/pages/publications/0026646947

UR - https://www.scopus.com/pages/publications/0026646947#tab=citedBy

U2 - 10.1016/S0040-4039(00)61267-4

DO - 10.1016/S0040-4039(00)61267-4

M3 - Article

AN - SCOPUS:0026646947

SN - 0040-4039

VL - 33

SP - 4717

EP - 4720

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 33

ER -

Friedel-Crafts cyclization of 2-(3-indolythio)propionic acids. An unusual rearrangement leading to 4-sulfur-substituted tricyclic indoles

Abstract

All Science Journal Classification (ASJC) codes

Keywords

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