Synthesis of polyazamacrocyclic compounds via modified Richman-Atkins cyclization of β-trimethylsilylethanesulfonamides

R. C. Hoye; R. C. Hoye; J. E. Richman; G. A. Dantas; M. F. Lightbourne; L. Scott Shinneman

doi:10.1021/jo001639o

Synthesis of polyazamacrocyclic compounds via modified Richman-Atkins cyclization of β-trimethylsilylethanesulfonamides

R. C. Hoye, R. C. Hoye, J. E. Richman, G. A. Dantas, M. F. Lightbourne, L. Scott Shinneman

Biotechnology Institute

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37 Scopus citations

Abstract

The Richman-Atkins cyclization remains one of the most widely used methods for the preparation of macrocyclic polyamines. The use of β-trimethylsilylethanesulfonamides (SES-sulfonamides) for the preparation of polyazamacrocyclic compounds is described. This expands existing Richman-Atkins sulfonamide macrocyclization methodology, and it successfully enables preparation of labile polyaza[n](1,4)naphthalenophanes and polyaza[n](9,10)anthracenophanes, not previously available in appreciable quantities.

Original language	English (US)
Pages (from-to)	2722-2725
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	66
Issue number	8
DOIs	https://doi.org/10.1021/jo001639o
State	Published - Apr 20 2001

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title = "Synthesis of polyazamacrocyclic compounds via modified Richman-Atkins cyclization of β-trimethylsilylethanesulfonamides",

abstract = "The Richman-Atkins cyclization remains one of the most widely used methods for the preparation of macrocyclic polyamines. The use of β-trimethylsilylethanesulfonamides (SES-sulfonamides) for the preparation of polyazamacrocyclic compounds is described. This expands existing Richman-Atkins sulfonamide macrocyclization methodology, and it successfully enables preparation of labile polyaza[n](1,4)naphthalenophanes and polyaza[n](9,10)anthracenophanes, not previously available in appreciable quantities.",

author = "Hoye, {R. C.} and Hoye, {R. C.} and Richman, {J. E.} and Dantas, {G. A.} and Lightbourne, {M. F.} and {Scott Shinneman}, L.",

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doi = "10.1021/jo001639o",

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AU - Dantas, G. A.

AU - Lightbourne, M. F.

AU - Scott Shinneman, L.

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AB - The Richman-Atkins cyclization remains one of the most widely used methods for the preparation of macrocyclic polyamines. The use of β-trimethylsilylethanesulfonamides (SES-sulfonamides) for the preparation of polyazamacrocyclic compounds is described. This expands existing Richman-Atkins sulfonamide macrocyclization methodology, and it successfully enables preparation of labile polyaza[n](1,4)naphthalenophanes and polyaza[n](9,10)anthracenophanes, not previously available in appreciable quantities.

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Synthesis of polyazamacrocyclic compounds via modified Richman-Atkins cyclization of β-trimethylsilylethanesulfonamides

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