title: Synthesis of Novel 5,6-Disubstituted Pyrrolo [2,3-d]Pyrimidine-2,4-Diones Via One-Pot Three-Component Reactions.
abstract: A simple and novel method for the synthesis of 5,6-disubstituted pyrrolo[2,3-d]pyrimidine-2,4-diones has been reported using arylglyoxal-based three-component reactions. Under microwave heating conditions, arylglyoxal, 6-amino uracil, or its derivatives reacts with various thiols in acetic acid medium to provide a series of pyrrolo[2,3-d]pyrimidine-2,4-diones (4) having a thioether and an aryl ring in 5 and 6 positions, respectively. On the other hand reaction of arylglyoxal, amino uracil and malononitrile in place of thiols, provided corresponding 5,6-disubstituted pyrrolo[2,3-d]pyrimidine-2,4-diones (5) with selectively converting one of the -CN to -CONH2group both in conventional (method A) and microwave heating conditions (method B). This methodology is a simple and efficient protocol for the synthesis of diverse 5,6-disubstituted pyrrolo[2,3-d]pyrimidine-2,4-diones from the readily available starting materials in good yields.
authors.affiliation: Department of Chemistry, Indian Institute of Technology Patna , Bihar, Patna-8001103, India.|Department of Chemistry, Rayalaseema University , Kurnool, Andhra Pradesh-518007, India.
authors.forename: Shaik
authors.initials: S
authors.lastname: Karamthulla
authors.affiliation: Department of Chemistry, Indian Institute of Technology Patna , Bihar, Patna-8001103, India.
authors.forename: Asim
authors.initials: A
authors.lastname: Jana
authors.affiliation: Department of Chemistry, Indian Institute of Technology Patna , Bihar, Patna-8001103, India.
authors.forename: Lokman H
authors.identifier: 0000-0003-1735-1985
authors.initials: LH
authors.lastname: Choudhury
mesh_terms: D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D008872:Microwaves; D009570:Nitriles / Q000138:chemical synthesis / Q000737:chemistry; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis / Q000737:chemistry; D014498:Uracil / Q000031:analogs & derivatives / Q000138:chemical synthesis
chemical_list: D009570:Nitriles; D011743:Pyrimidines; D011758:Pyrroles; C450639:Pyrrolo(2,3-d)pyrimidine; D013438:Sulfhydryl Compounds; D014498:Uracil; C000945:dicyanmethane
keywords: 5,6-disubstituted pyrrolo[2,3-d]pyrimidines; 6-aminouracil derivatives; arylglyoxal monohydrates; malononitrile; microwave-assisted reactions; thiols