Novel spiro and fused heterocycles from the allylation of indigo

Mohammed K. Abdel-Hamid; John B. Bremner; Jonathan Coates; Paul A. Keller; Celia Miländer; Yasmine S. Torkamani; Brian W. Skelton; Allan H. White; Anthony C. Willis

doi:10.1016/j.tetlet.2009.09.098

Novel spiro and fused heterocycles from the allylation of indigo

Mohammed K. Abdel-Hamid
, John B. Bremner^*
, Jonathan Coates
, Paul A. Keller
, Celia Miländer
, Yasmine S. Torkamani
, Brian W. Skelton
, Allan H. White
, Anthony C. Willis

^*Corresponding author for this work

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

16 Citations (Scopus)

Abstract

The allylation of indigo results in the one-step synthesis of two unique complex heterocyclic systems: a spiroindoline-pyridoindolone arising from the addition of three allyl moieties and a fused pyridoindolo-azepinoindolone generated from the addition and subsequent cyclisation of two allyl moieties. The structures of these novel heterocycles are assigned unambiguously using extensive NMR experiments and by X-ray crystallographic analysis. The distribution of the products is influenced by the use of thermal versus microwave heating. Crown

Original language	English
Pages (from-to)	6947-6950
Number of pages	4
Journal	Tetrahedron Letters
Volume	50
Issue number	50
DOIs	https://doi.org/10.1016/j.tetlet.2009.09.098
Publication status	Published - 16 Dec 2009

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10.1016/j.tetlet.2009.09.098

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title = "Novel spiro and fused heterocycles from the allylation of indigo",

abstract = "The allylation of indigo results in the one-step synthesis of two unique complex heterocyclic systems: a spiroindoline-pyridoindolone arising from the addition of three allyl moieties and a fused pyridoindolo-azepinoindolone generated from the addition and subsequent cyclisation of two allyl moieties. The structures of these novel heterocycles are assigned unambiguously using extensive NMR experiments and by X-ray crystallographic analysis. The distribution of the products is influenced by the use of thermal versus microwave heating. Crown",

keywords = "Azepinoindolone, Domino reaction, Indigo, Pyridoindolone, Spiroindoline",

author = "Abdel-Hamid, \{Mohammed K.\} and Bremner, \{John B.\} and Jonathan Coates and Keller, \{Paul A.\} and Celia Mil{\"a}nder and Torkamani, \{Yasmine S.\} and Skelton, \{Brian W.\} and White, \{Allan H.\} and Willis, \{Anthony C.\}",

year = "2009",

month = dec,

day = "16",

doi = "10.1016/j.tetlet.2009.09.098",

language = "English",

volume = "50",

pages = "6947--6950",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Novel spiro and fused heterocycles from the allylation of indigo

AU - Abdel-Hamid, Mohammed K.

AU - Bremner, John B.

AU - Coates, Jonathan

AU - Keller, Paul A.

AU - Miländer, Celia

AU - Torkamani, Yasmine S.

AU - Skelton, Brian W.

AU - White, Allan H.

AU - Willis, Anthony C.

PY - 2009/12/16

Y1 - 2009/12/16

N2 - The allylation of indigo results in the one-step synthesis of two unique complex heterocyclic systems: a spiroindoline-pyridoindolone arising from the addition of three allyl moieties and a fused pyridoindolo-azepinoindolone generated from the addition and subsequent cyclisation of two allyl moieties. The structures of these novel heterocycles are assigned unambiguously using extensive NMR experiments and by X-ray crystallographic analysis. The distribution of the products is influenced by the use of thermal versus microwave heating. Crown

AB - The allylation of indigo results in the one-step synthesis of two unique complex heterocyclic systems: a spiroindoline-pyridoindolone arising from the addition of three allyl moieties and a fused pyridoindolo-azepinoindolone generated from the addition and subsequent cyclisation of two allyl moieties. The structures of these novel heterocycles are assigned unambiguously using extensive NMR experiments and by X-ray crystallographic analysis. The distribution of the products is influenced by the use of thermal versus microwave heating. Crown

KW - Azepinoindolone

KW - Domino reaction

KW - Indigo

KW - Pyridoindolone

KW - Spiroindoline

UR - https://www.scopus.com/pages/publications/70350519042

U2 - 10.1016/j.tetlet.2009.09.098

DO - 10.1016/j.tetlet.2009.09.098

M3 - Article

SN - 0040-4039

VL - 50

SP - 6947

EP - 6950

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 50

ER -

Novel spiro and fused heterocycles from the allylation of indigo

Abstract

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