Tandem inverse electron demand Diels-Alder, retro Diels-Alder and intramolecular Diels-Alder sequences: one-pot synthesis of diaza-polycycles

William Bromley; Mairi Gibson; Stuart Lang; Steven Raw; Adrian Whitwood; Richard Taylor

doi:10.1016/j.tet.2007.02.056

Tandem inverse electron demand Diels-Alder, retro Diels-Alder and intramolecular Diels-Alder sequences: one-pot synthesis of diaza-polycycles

William Bromley, Mairi Gibson, Stuart Lang, Steven Raw, Adrian Whitwood, Richard Taylor

Pure And Applied Chemistry

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

30 Citations (Scopus)

Abstract

A new and straightforward methodology is described for the construction of complex nitrogen-containing polycycles from substituted 1,2,4-triazines and enamines, prepared in situ from carbonyl components and allylic amines. The transformation proceeds via a pericyclic reaction cascade (inverse electron demand Diels-Alder then retro Diels-Alder then intramolecular Diels-Alder) forming the polycyclic systems in good to excellent yield and with high diastereoselectivity in a one-pot procedure. The scope and limitations of the methodology are discribed as are preliminary studies to extend its synthetic utilitiy.

Original language	English
Pages (from-to)	6004-6014
Number of pages	11
Journal	Tetrahedron
Volume	63
Issue number	26
Early online date	20 Feb 2007
DOIs	https://doi.org/10.1016/j.tet.2007.02.056
Publication status	Published - 25 Jun 2007

Keywords

substituted 1,2,4-triazines
Diels-Alder reactions
inverse electron demand
IMDA
cascade or tandem processes
diaza-polycycles

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10.1016/j.tet.2007.02.056

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title = "Tandem inverse electron demand Diels-Alder, retro Diels-Alder and intramolecular Diels-Alder sequences: one-pot synthesis of diaza-polycycles",

abstract = "A new and straightforward methodology is described for the construction of complex nitrogen-containing polycycles from substituted 1,2,4-triazines and enamines, prepared in situ from carbonyl components and allylic amines. The transformation proceeds via a pericyclic reaction cascade (inverse electron demand Diels-Alder then retro Diels-Alder then intramolecular Diels-Alder) forming the polycyclic systems in good to excellent yield and with high diastereoselectivity in a one-pot procedure. The scope and limitations of the methodology are discribed as are preliminary studies to extend its synthetic utilitiy.",

keywords = "substituted 1,2,4-triazines, Diels-Alder reactions , inverse electron demand, IMDA, cascade or tandem processes, diaza-polycycles",

author = "William Bromley and Mairi Gibson and Stuart Lang and Steven Raw and Adrian Whitwood and Richard Taylor",

year = "2007",

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day = "25",

doi = "10.1016/j.tet.2007.02.056",

language = "English",

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journal = "Tetrahedron",

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TY - JOUR

T1 - Tandem inverse electron demand Diels-Alder, retro Diels-Alder and intramolecular Diels-Alder sequences

T2 - one-pot synthesis of diaza-polycycles

AU - Bromley, William

AU - Gibson, Mairi

AU - Lang, Stuart

AU - Raw, Steven

AU - Whitwood, Adrian

AU - Taylor, Richard

PY - 2007/6/25

Y1 - 2007/6/25

N2 - A new and straightforward methodology is described for the construction of complex nitrogen-containing polycycles from substituted 1,2,4-triazines and enamines, prepared in situ from carbonyl components and allylic amines. The transformation proceeds via a pericyclic reaction cascade (inverse electron demand Diels-Alder then retro Diels-Alder then intramolecular Diels-Alder) forming the polycyclic systems in good to excellent yield and with high diastereoselectivity in a one-pot procedure. The scope and limitations of the methodology are discribed as are preliminary studies to extend its synthetic utilitiy.

AB - A new and straightforward methodology is described for the construction of complex nitrogen-containing polycycles from substituted 1,2,4-triazines and enamines, prepared in situ from carbonyl components and allylic amines. The transformation proceeds via a pericyclic reaction cascade (inverse electron demand Diels-Alder then retro Diels-Alder then intramolecular Diels-Alder) forming the polycyclic systems in good to excellent yield and with high diastereoselectivity in a one-pot procedure. The scope and limitations of the methodology are discribed as are preliminary studies to extend its synthetic utilitiy.

KW - substituted 1,2,4-triazines

KW - Diels-Alder reactions

KW - inverse electron demand

KW - IMDA

KW - cascade or tandem processes

KW - diaza-polycycles

U2 - 10.1016/j.tet.2007.02.056

DO - 10.1016/j.tet.2007.02.056

M3 - Article

VL - 63

SP - 6004

EP - 6014

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 26

ER -