Efficient synthesis of 1,3,7-substituted xanthines by a safety-catch protection strategy

Matthew Allwood; Boorna Cannan; Daan M. F. van Aalten; Ian M. Eggleston

doi:10.1016/j.tet.2007.09.067

Efficient synthesis of 1,3,7-substituted xanthines by a safety-catch protection strategy

Matthew Allwood, Boorna Cannan, Daan M. F. van Aalten, Ian M. Eggleston

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

22 Citations (Scopus)

Abstract

An efficient synthesis of selectively N-substituted xanthine derivatives is described. Cyclocondensation of a suitably protected ammoimidazole with methyl-2-phenylthioethyl carbamate, followed by oxidation of sulfur to the sulfone, provides access to an orthogonally 1,7-protected xanthine, which may then be regioselectively alkylated and deprotected under mild conditions. (c) 2007 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	12294-12302
Number of pages	9
Journal	Tetrahedron
Volume	63
Issue number	50
DOIs	https://doi.org/10.1016/j.tet.2007.09.067
Publication status	Published - 10 Dec 2007

Keywords

Solid phase synthesis
Receptor antagonists
1,3-substituted xanthines
Theophylline
Derivatives
Inhibitors
Expression
Asthma
Potent

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10.1016/j.tet.2007.09.067

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title = "Efficient synthesis of 1,3,7-substituted xanthines by a safety-catch protection strategy",

abstract = "An efficient synthesis of selectively N-substituted xanthine derivatives is described. Cyclocondensation of a suitably protected ammoimidazole with methyl-2-phenylthioethyl carbamate, followed by oxidation of sulfur to the sulfone, provides access to an orthogonally 1,7-protected xanthine, which may then be regioselectively alkylated and deprotected under mild conditions. (c) 2007 Elsevier Ltd. All rights reserved.",

keywords = "Solid phase synthesis, Receptor antagonists, 1,3-substituted xanthines, Theophylline, Derivatives, Inhibitors, Expression, Asthma, Potent",

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T1 - Efficient synthesis of 1,3,7-substituted xanthines by a safety-catch protection strategy

AU - Allwood, Matthew

AU - Cannan, Boorna

AU - van Aalten, Daan M. F.

AU - Eggleston, Ian M.

PY - 2007/12/10

Y1 - 2007/12/10

N2 - An efficient synthesis of selectively N-substituted xanthine derivatives is described. Cyclocondensation of a suitably protected ammoimidazole with methyl-2-phenylthioethyl carbamate, followed by oxidation of sulfur to the sulfone, provides access to an orthogonally 1,7-protected xanthine, which may then be regioselectively alkylated and deprotected under mild conditions. (c) 2007 Elsevier Ltd. All rights reserved.

AB - An efficient synthesis of selectively N-substituted xanthine derivatives is described. Cyclocondensation of a suitably protected ammoimidazole with methyl-2-phenylthioethyl carbamate, followed by oxidation of sulfur to the sulfone, provides access to an orthogonally 1,7-protected xanthine, which may then be regioselectively alkylated and deprotected under mild conditions. (c) 2007 Elsevier Ltd. All rights reserved.

KW - Solid phase synthesis

KW - Receptor antagonists

KW - 1,3-substituted xanthines

KW - Theophylline

KW - Derivatives

KW - Inhibitors

KW - Expression

KW - Asthma

KW - Potent

U2 - 10.1016/j.tet.2007.09.067

DO - 10.1016/j.tet.2007.09.067

M3 - Article

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VL - 63

SP - 12294

EP - 12302

JO - Tetrahedron

JF - Tetrahedron

IS - 50

ER -

Efficient synthesis of 1,3,7-substituted xanthines by a safety-catch protection strategy

Abstract

Keywords

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