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

TY - JOUR

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

SN - 0040-4020

VL - 63

SP - 12294

EP - 12302

JO - Tetrahedron

JF - Tetrahedron

IS - 50

ER -