New N-acyl, N-alkyl, and N-bridged derivatives of rac-6,6′,7,7′-tetramethoxy-1,1′,2,2′,3,3′,4, 4′-octahydro-1,1′-bisisoquinoline

Stephan Busato; Donald C. Craig; Zaher M.A. Judeh; Roger W. Read

doi:10.1016/S0040-4020(02)01535-1

New N-acyl, N-alkyl, and N-bridged derivatives of rac-6,6′,7,7′-tetramethoxy-1,1′,2,2′,3,3′,4, 4′-octahydro-1,1′-bisisoquinoline

Stephan Busato, Donald C. Craig, Zaher M.A. Judeh, Roger W. Read

University of New South Wales

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

24 Citations (Scopus)

Abstract

The preparation of potential new ligand systems based on the rac-1,1′,2,2′,3,3′,4,4′-octahydro-6,6′,7, 7′-tetramethoxy-1,1′-bisisoquinoline skeleton has been investigated. Syntheses of N-(2-bromobenzyl), N-(3-acetoxybenzyl), N-acetyl, N-chloroacetyl, N-chlorocarbonyl, N-ethoxycarbonyl and N-tert-butyloxycarbonyl derivatives and five macrocyclic, polyether containing derivatives are described.

Original language	English
Pages (from-to)	461-472
Number of pages	12
Journal	Tetrahedron
Volume	59
Issue number	4
DOIs	https://doi.org/10.1016/S0040-4020(02)01535-1
Publication status	Published - Jan 20 2003
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
Drug Discovery
Organic Chemistry

Keywords

1,1′-bisisoquinolines
Asymmetric reduction
Crown ethers
Ligands
Macrocycles
NMR spectroscopy

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10.1016/S0040-4020(02)01535-1

Cite this

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title = "New N-acyl, N-alkyl, and N-bridged derivatives of rac-6,6′,7,7′-tetramethoxy-1,1′,2,2′,3,3′,4, 4′-octahydro-1,1′-bisisoquinoline",

abstract = "The preparation of potential new ligand systems based on the rac-1,1′,2,2′,3,3′,4,4′-octahydro-6,6′,7, 7′-tetramethoxy-1,1′-bisisoquinoline skeleton has been investigated. Syntheses of N-(2-bromobenzyl), N-(3-acetoxybenzyl), N-acetyl, N-chloroacetyl, N-chlorocarbonyl, N-ethoxycarbonyl and N-tert-butyloxycarbonyl derivatives and five macrocyclic, polyether containing derivatives are described.",

keywords = "1,1′-bisisoquinolines, Asymmetric reduction, Crown ethers, Ligands, Macrocycles, NMR spectroscopy",

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doi = "10.1016/S0040-4020(02)01535-1",

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T1 - New N-acyl, N-alkyl, and N-bridged derivatives of rac-6,6′,7,7′-tetramethoxy-1,1′,2,2′,3,3′,4, 4′-octahydro-1,1′-bisisoquinoline

AU - Busato, Stephan

AU - Craig, Donald C.

AU - Judeh, Zaher M.A.

AU - Read, Roger W.

PY - 2003/1/20

Y1 - 2003/1/20

N2 - The preparation of potential new ligand systems based on the rac-1,1′,2,2′,3,3′,4,4′-octahydro-6,6′,7, 7′-tetramethoxy-1,1′-bisisoquinoline skeleton has been investigated. Syntheses of N-(2-bromobenzyl), N-(3-acetoxybenzyl), N-acetyl, N-chloroacetyl, N-chlorocarbonyl, N-ethoxycarbonyl and N-tert-butyloxycarbonyl derivatives and five macrocyclic, polyether containing derivatives are described.

AB - The preparation of potential new ligand systems based on the rac-1,1′,2,2′,3,3′,4,4′-octahydro-6,6′,7, 7′-tetramethoxy-1,1′-bisisoquinoline skeleton has been investigated. Syntheses of N-(2-bromobenzyl), N-(3-acetoxybenzyl), N-acetyl, N-chloroacetyl, N-chlorocarbonyl, N-ethoxycarbonyl and N-tert-butyloxycarbonyl derivatives and five macrocyclic, polyether containing derivatives are described.

KW - 1,1′-bisisoquinolines

KW - Asymmetric reduction

KW - Crown ethers

KW - Ligands

KW - Macrocycles

KW - NMR spectroscopy

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U2 - 10.1016/S0040-4020(02)01535-1

DO - 10.1016/S0040-4020(02)01535-1

M3 - Article

AN - SCOPUS:0037454708

SN - 0040-4020

VL - 59

SP - 461

EP - 472

JO - Tetrahedron

JF - Tetrahedron

IS - 4

ER -

New N-acyl, N-alkyl, and N-bridged derivatives of rac-6,6′,7,7′-tetramethoxy-1,1′,2,2′,3,3′,4, 4′-octahydro-1,1′-bisisoquinoline

Abstract

ASJC Scopus Subject Areas

Keywords

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