N-Hydroxy indoles as flexible substrates in rearrangements - A novel reaction with activated triple bonds

Mariana P. Duarte; Ricardo F. Mendonça; Sundaresan Prabhakar; Ana Maria Lobo

doi:10.1016/j.tetlet.2005.12.021

N-Hydroxy indoles as flexible substrates in rearrangements - A novel reaction with activated triple bonds

Mariana P. Duarte, Ricardo F. Mendonça, Sundaresan Prabhakar, Ana Maria Lobo

DQ - Departamento de Química

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

8 Citations (Scopus)

Abstract

A novel rearrangement of N-hydroxy indole derivatives obtained from addition of N-hydroxy indoles to the activated triple bonds of alkynes was found to coexist with 3,3-sigmatropic rearrangements to the indolic ring. A mechanism involving an intermediate oxaziridinium ring rationalizes the transformation.

Original language	English
Pages (from-to)	1173-1176
Number of pages	4
Journal	Tetrahedron Letters
Volume	47
Issue number	7
DOIs	https://doi.org/10.1016/j.tetlet.2005.12.021
Publication status	Published - 13 Feb 2006

Keywords

Additions
N-Hydroxy indoles
Oxaziridinium
Rearrangements

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title = "N-Hydroxy indoles as flexible substrates in rearrangements - A novel reaction with activated triple bonds",

abstract = "A novel rearrangement of N-hydroxy indole derivatives obtained from addition of N-hydroxy indoles to the activated triple bonds of alkynes was found to coexist with 3,3-sigmatropic rearrangements to the indolic ring. A mechanism involving an intermediate oxaziridinium ring rationalizes the transformation.",

keywords = "Additions, N-Hydroxy indoles, Oxaziridinium, Rearrangements",

author = "Duarte, \{Mariana P.\} and Mendon{\c c}a, \{Ricardo F.\} and Sundaresan Prabhakar and Lobo, \{Ana Maria\}",

year = "2006",

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day = "13",

doi = "10.1016/j.tetlet.2005.12.021",

language = "English",

volume = "47",

pages = "1173--1176",

journal = "Tetrahedron Letters",

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T1 - N-Hydroxy indoles as flexible substrates in rearrangements - A novel reaction with activated triple bonds

AU - Duarte, Mariana P.

AU - Mendonça, Ricardo F.

AU - Prabhakar, Sundaresan

AU - Lobo, Ana Maria

PY - 2006/2/13

Y1 - 2006/2/13

N2 - A novel rearrangement of N-hydroxy indole derivatives obtained from addition of N-hydroxy indoles to the activated triple bonds of alkynes was found to coexist with 3,3-sigmatropic rearrangements to the indolic ring. A mechanism involving an intermediate oxaziridinium ring rationalizes the transformation.

AB - A novel rearrangement of N-hydroxy indole derivatives obtained from addition of N-hydroxy indoles to the activated triple bonds of alkynes was found to coexist with 3,3-sigmatropic rearrangements to the indolic ring. A mechanism involving an intermediate oxaziridinium ring rationalizes the transformation.

KW - Additions

KW - N-Hydroxy indoles

KW - Oxaziridinium

KW - Rearrangements

UR - https://www.scopus.com/pages/publications/30544435348

U2 - 10.1016/j.tetlet.2005.12.021

DO - 10.1016/j.tetlet.2005.12.021

M3 - Article

SN - 0040-4039

VL - 47

SP - 1173

EP - 1176

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 7

ER -

N-Hydroxy indoles as flexible substrates in rearrangements - A novel reaction with activated triple bonds

Abstract

Keywords

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