Novel spiro fused heterocycles from the allylation of indigo

M.K. Abdel-Hamid; J.B. Bremner; J. Coates; P.A. Keller; C. Milander; Y.S. Torkamani; Brian Skelton; Allan White; A.C. Willis

doi:10.1016/j.tetlet.2009.09.098

Novel spiro fused heterocycles from the allylation of indigo

M.K. Abdel-Hamid, J.B. Bremner, J. Coates, P.A. Keller, C. Milander, Y.S. Torkamani, Brian Skelton, Allan White, A.C. Willis

School of Molecular Sciences

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

14 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.

Original language	English
Pages (from-to)	6947-6950
Journal	Tetrahedron Letters
Volume	50
DOIs	https://doi.org/10.1016/j.tetlet.2009.09.098
Publication status	Published - 2009

Access to Document

10.1016/j.tetlet.2009.09.098

Cite this

@article{619cb572c80a4f4888dbf240983bf93b,

title = "Novel spiro 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.",

author = "M.K. Abdel-Hamid and J.B. Bremner and J. Coates and P.A. Keller and C. Milander and Y.S. Torkamani and Brian Skelton and Allan White and A.C. Willis",

year = "2009",

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

language = "English",

volume = "50",

pages = "6947--6950",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Pergamon",

}

TY - JOUR

T1 - Novel spiro fused heterocycles from the allylation of indigo

AU - Abdel-Hamid, M.K.

AU - Bremner, J.B.

AU - Coates, J.

AU - Keller, P.A.

AU - Milander, C.

AU - Torkamani, Y.S.

AU - Skelton, Brian

AU - White, Allan

AU - Willis, A.C.

PY - 2009

Y1 - 2009

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.

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.

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

ER -

Novel spiro fused heterocycles from the allylation of indigo

Abstract

Access to Document

Fingerprint

Cite this