Swern oxidation of tryptamine derivatives

Patrick D. Bailey; Philip J. Cochrane; Frances Irvine; Keith M. Morgan; D. P J Pearson; Kenneth T. Veal

doi:10.1016/S0040-4039(99)00692-9

Swern oxidation of tryptamine derivatives

Patrick D. Bailey, Philip J. Cochrane, Frances Irvine, Keith M. Morgan, D. P J Pearson, Kenneth T. Veal

School of Engineering & Physical Sciences

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

19 Citations (Scopus)

Abstract

The Swern oxidation of various indolic substrates is described, and a range of products resulting from overall oxidation at the 2-position were observed. In particular, depending on the substrate and reaction conditions, it was possible to achieve direct oxidation to a, ß-unsaturated systems at the 2-position, to introduce a nucleophile at the 2-position, and to introduce a CH₃-S-CH₂ group at the indole 4-position via an unprecedented rearrangement of a Swern intermediate.

Original language	English
Pages (from-to)	4593-4596
Number of pages	4
Journal	Tetrahedron Letters
Volume	40
Issue number	24
DOIs	https://doi.org/10.1016/S0040-4039(99)00692-9
Publication status	Published - 11 Jun 1999

Keywords

Indoles
Oxidation
Rearrangements
Swern

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10.1016/S0040-4039(99)00692-9

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title = "Swern oxidation of tryptamine derivatives",

abstract = "The Swern oxidation of various indolic substrates is described, and a range of products resulting from overall oxidation at the 2-position were observed. In particular, depending on the substrate and reaction conditions, it was possible to achieve direct oxidation to a, {\ss}-unsaturated systems at the 2-position, to introduce a nucleophile at the 2-position, and to introduce a CH3-S-CH2 group at the indole 4-position via an unprecedented rearrangement of a Swern intermediate.",

keywords = "Indoles, Oxidation, Rearrangements, Swern",

author = "Bailey, {Patrick D.} and Cochrane, {Philip J.} and Frances Irvine and Morgan, {Keith M.} and Pearson, {D. P J} and Veal, {Kenneth T.}",

year = "1999",

month = jun,

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doi = "10.1016/S0040-4039(99)00692-9",

language = "English",

volume = "40",

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journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Swern oxidation of tryptamine derivatives

AU - Bailey, Patrick D.

AU - Cochrane, Philip J.

AU - Irvine, Frances

AU - Morgan, Keith M.

AU - Pearson, D. P J

AU - Veal, Kenneth T.

PY - 1999/6/11

Y1 - 1999/6/11

N2 - The Swern oxidation of various indolic substrates is described, and a range of products resulting from overall oxidation at the 2-position were observed. In particular, depending on the substrate and reaction conditions, it was possible to achieve direct oxidation to a, ß-unsaturated systems at the 2-position, to introduce a nucleophile at the 2-position, and to introduce a CH3-S-CH2 group at the indole 4-position via an unprecedented rearrangement of a Swern intermediate.

AB - The Swern oxidation of various indolic substrates is described, and a range of products resulting from overall oxidation at the 2-position were observed. In particular, depending on the substrate and reaction conditions, it was possible to achieve direct oxidation to a, ß-unsaturated systems at the 2-position, to introduce a nucleophile at the 2-position, and to introduce a CH3-S-CH2 group at the indole 4-position via an unprecedented rearrangement of a Swern intermediate.

KW - Indoles

KW - Oxidation

KW - Rearrangements

KW - Swern

UR - http://www.scopus.com/inward/record.url?scp=0033546353&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(99)00692-9

DO - 10.1016/S0040-4039(99)00692-9

M3 - Article

SN - 0040-4039

VL - 40

SP - 4593

EP - 4596

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 24

ER -

Swern oxidation of tryptamine derivatives

Abstract

Keywords

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