New and practical method for synthesis of 1- and 1,3-substituted xanthines. |
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| Authors: | Ilia A Zavialov Vilas H Dahanukar Hoa Nguyen Cecilia Orr Fucheng Zhang David R Andrews |
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| Institution: | Department of Synthetic Chemistry, Schering-Plough Research Institute, 1011 Morris Avenue, Union, New Jersey 07083, USA. |
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| Abstract: | reaction: see text] A new and practical method for the synthesis of 1- and 1,3-substituted xanthines is reported. Direct base-promoted condensation of the imidazole precursor 1 with carbamates 2 gives 1-substituted 7-PMB xanthines 7 in good yields. Alkylation of these derivatives or their potassium salts proceeds under mild conditions to give functionalized 1,3-substituted 7-PMB xanthines 9 in good to excellent yields. The obtained 7-PMB-protected derivatives can be readily deprotected to give the parent 1- and 1,3-substituted xanthines. |
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