Synthesis and conformational behaviour of tetra-anthranilides

Alireza Hoorfar; W. David Ollis; J. Fraser Stoddart; David J. Williams

doi:10.1016/S0040-4039(00)93691-8

Synthesis and conformational behaviour of tetra-anthranilides

Alireza Hoorfar^*, W. David Ollis, J. Fraser Stoddart, David J. Williams

^*Corresponding author for this work

Chemistry

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5 Scopus citations

Abstract

The tetra-anthranilide derivatives (5)-(7) have been synthesised. X-Ray crystallography shows that N,N′,N″-trimethyltetra-anthranilide (5) adopts a conformation with three trans - and one cis-amide linkages in the solid state. Dynamic ¹H n.m.r. spectroscopy indicates that N-benzyl-N′,N″,N′″-trimethyltetra-anthranilide (7) exists as an interconverting ternary mixture of chiral non-planar conformational diastereoisomers in solution.

Original language	English (US)
Pages (from-to)	4211-4214
Number of pages	4
Journal	Tetrahedron Letters
Volume	21
Issue number	43
DOIs	https://doi.org/10.1016/S0040-4039(00)93691-8
State	Published - 1980

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Synthesis and conformational behaviour of tetra-anthranilides",

abstract = "The tetra-anthranilide derivatives (5)-(7) have been synthesised. X-Ray crystallography shows that N,N′,N″-trimethyltetra-anthranilide (5) adopts a conformation with three trans - and one cis-amide linkages in the solid state. Dynamic 1H n.m.r. spectroscopy indicates that N-benzyl-N′,N″,N′″-trimethyltetra-anthranilide (7) exists as an interconverting ternary mixture of chiral non-planar conformational diastereoisomers in solution.",

author = "Alireza Hoorfar and {David Ollis}, W. and {Fraser Stoddart}, J. and Williams, {David J.}",

year = "1980",

doi = "10.1016/S0040-4039(00)93691-8",

language = "English (US)",

volume = "21",

pages = "4211--4214",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

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TY - JOUR

T1 - Synthesis and conformational behaviour of tetra-anthranilides

AU - Hoorfar, Alireza

AU - David Ollis, W.

AU - Fraser Stoddart, J.

AU - Williams, David J.

PY - 1980

Y1 - 1980

N2 - The tetra-anthranilide derivatives (5)-(7) have been synthesised. X-Ray crystallography shows that N,N′,N″-trimethyltetra-anthranilide (5) adopts a conformation with three trans - and one cis-amide linkages in the solid state. Dynamic 1H n.m.r. spectroscopy indicates that N-benzyl-N′,N″,N′″-trimethyltetra-anthranilide (7) exists as an interconverting ternary mixture of chiral non-planar conformational diastereoisomers in solution.

AB - The tetra-anthranilide derivatives (5)-(7) have been synthesised. X-Ray crystallography shows that N,N′,N″-trimethyltetra-anthranilide (5) adopts a conformation with three trans - and one cis-amide linkages in the solid state. Dynamic 1H n.m.r. spectroscopy indicates that N-benzyl-N′,N″,N′″-trimethyltetra-anthranilide (7) exists as an interconverting ternary mixture of chiral non-planar conformational diastereoisomers in solution.

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U2 - 10.1016/S0040-4039(00)93691-8

DO - 10.1016/S0040-4039(00)93691-8

M3 - Article

AN - SCOPUS:9444232334

SN - 0040-4039

VL - 21

SP - 4211

EP - 4214

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 43

ER -

Synthesis and conformational behaviour of tetra-anthranilides

Abstract

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