174518-99-1

Upstream product

• 1866-38-2 m-Chlorocinnamic acid 
• 146830-75-3 5,6-diamino-3-prop-2-ynyl-1H,3H-pyrimidine-2,4-dione 
• 138895-22-4 6-amino-3-prop-2-ynyl-1H,3H-pyrimidine-2,4-dione 
• 146830-70-8 6-amino-5-nitroso-3-prop-2-ynyl-1H,3H-pyrimidine-2,4-dione 

Downstream Products

• 174519-04-1 (E)-N-(6-Amino-2,4-dioxo-1-propyl-3-prop-2-ynyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-3-(3-chloro-phenyl)-acrylamide 
• 174519-11-0 3-Benzyl-8-[(E)-2-(3-chloro-phenyl)-vinyl]-1-prop-2-ynyl-3,7-dihydro-purine-2,6-dione 
• 174519-10-9 8-[(E)-2-(3-Chloro-phenyl)-vinyl]-3-isobutyl-1-prop-2-ynyl-3,7-dihydro-purine-2,6-dione 
• 174519-09-6 8-[(E)-2-(3-Chloro-phenyl)-vinyl]-3-propyl-1-prop-2-ynyl-3,7-dihydro-purine-2,6-dione 
• 174519-08-5 8-[(E)-2-(3-Chloro-phenyl)-vinyl]-3-methyl-1-prop-2-ynyl-3,7-dihydro-purine-2,6-dione 
• 174519-02-9 (E)-N-(6-Amino-1-methyl-2,4-dioxo-3-prop-2-ynyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-3-(3-chloro-phenyl)-acrylamide 
• 174519-05-2 (E)-N-(6-Amino-1-benzyl-2,4-dioxo-3-prop-2-ynyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-3-(3-chloro-phenyl)-acrylamide 

Relevant academic research and scientific papers

A new versatile synthesis of xanthines with variable substituents in the 1-, 3-, 7- and 8-positions

A new convenient procedure for the synthesis of a wide range of xanthines has been developed starting from 3-substituted 6-aminouracils. Nitrosation and reduction yields the corresponding 5,6-diaminouracils, which are condensed with carboxylic acids. The resulting amides can be selectively alkylated at the uracil ring nitrogen N-1 (corresponding to xanthine N-3) under mild conditions. Ring closure and, if desired, alkylation at the 7-position, yields di-, tri-, or tetrasubstituted xanthines in high yields. Sensitive substituents, such as prop-2-ynyl, can be introduced in the 1-position. Variation of the 3-substituent is considerably facilitated in comparison with the standard procedure for the preparation of xanthines.