SYNTHETIC APPROACHES TO NORTROPANES AND NORTROP-6-ENES - INTRAMOLECULAR DISPLACEMENT BY NITROGEN IN 7-MEMBERED RINGS

A NAYLOR, N HOWARTH, J R MALPASS

Research output: Contribution to journalArticle

Abstract

The synthesis of simple nortropane and nortrop-6-ene derivatives from cyclohepta-1,3-diene is described. The key intermediates are trans-1-amino-4-chloro-cycloheptanes and -cyclohept-2-enes which are derived efficiently from the corresponding cis-amino-alcohols and undergo intramolecular cyclisation. Corresponding derivatisation of cyclohexa- and cycloocta-1,3-dienes is explored and attempts to achieve Pd-catalysed cyclisation of 1-amino-4-acetoxy-derivatives is described. Nitrogen inversion data for selected nortropane derivatives are included.

Original languageEnglish
Pages (from-to)451-468
Number of pages18
JournalTetrahedron
Volume49
Issue number2
Publication statusPublished - 8 Jan 1993

Cite this

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title = "SYNTHETIC APPROACHES TO NORTROPANES AND NORTROP-6-ENES - INTRAMOLECULAR DISPLACEMENT BY NITROGEN IN 7-MEMBERED RINGS",
abstract = "The synthesis of simple nortropane and nortrop-6-ene derivatives from cyclohepta-1,3-diene is described. The key intermediates are trans-1-amino-4-chloro-cycloheptanes and -cyclohept-2-enes which are derived efficiently from the corresponding cis-amino-alcohols and undergo intramolecular cyclisation. Corresponding derivatisation of cyclohexa- and cycloocta-1,3-dienes is explored and attempts to achieve Pd-catalysed cyclisation of 1-amino-4-acetoxy-derivatives is described. Nitrogen inversion data for selected nortropane derivatives are included.",
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SYNTHETIC APPROACHES TO NORTROPANES AND NORTROP-6-ENES - INTRAMOLECULAR DISPLACEMENT BY NITROGEN IN 7-MEMBERED RINGS. / NAYLOR, A ; HOWARTH, N ; MALPASS, J R .

In: Tetrahedron, Vol. 49, No. 2, 08.01.1993, p. 451-468.

Research output: Contribution to journalArticle

TY - JOUR

T1 - SYNTHETIC APPROACHES TO NORTROPANES AND NORTROP-6-ENES - INTRAMOLECULAR DISPLACEMENT BY NITROGEN IN 7-MEMBERED RINGS

AU - NAYLOR, A

AU - HOWARTH, N

AU - MALPASS, J R

PY - 1993/1/8

Y1 - 1993/1/8

N2 - The synthesis of simple nortropane and nortrop-6-ene derivatives from cyclohepta-1,3-diene is described. The key intermediates are trans-1-amino-4-chloro-cycloheptanes and -cyclohept-2-enes which are derived efficiently from the corresponding cis-amino-alcohols and undergo intramolecular cyclisation. Corresponding derivatisation of cyclohexa- and cycloocta-1,3-dienes is explored and attempts to achieve Pd-catalysed cyclisation of 1-amino-4-acetoxy-derivatives is described. Nitrogen inversion data for selected nortropane derivatives are included.

AB - The synthesis of simple nortropane and nortrop-6-ene derivatives from cyclohepta-1,3-diene is described. The key intermediates are trans-1-amino-4-chloro-cycloheptanes and -cyclohept-2-enes which are derived efficiently from the corresponding cis-amino-alcohols and undergo intramolecular cyclisation. Corresponding derivatisation of cyclohexa- and cycloocta-1,3-dienes is explored and attempts to achieve Pd-catalysed cyclisation of 1-amino-4-acetoxy-derivatives is described. Nitrogen inversion data for selected nortropane derivatives are included.

M3 - Article

VL - 49

SP - 451

EP - 468

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 2

ER -