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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 36, 2006 - Issue 23
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Original Articles

Reactions of 6‐Aminouracils: The First Simple, Fast, and Highly Efficient Synthesis of bis(6‐Aminopyrimidonyl)methanes (BAPMs) Using Thermal or Microwave‐Assisted Solvent‐Free Methods

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Pages 3631-3638 | Received 02 Feb 2006, Published online: 24 Nov 2006

References

  • Figueroa‐Villar , J. D. , Carneiro , C. L. and Cruz , E. R. 1992 . Synthesis of 6‐phenylaminofuro [2,3‐d]pyrimidine‐2,4(1H,3H)‐diones from barbiturylbenzylidenes and isonitriles . Heterocycles , 34 : 891 – 894 .
  • Nugent , R. A. , Schlachter , S. T. , Murphy , M. J. , Cleek , G. J. , Poel , T. J. , Wishka , D. G. , Graber , D. R. , Yogi , Y. , Kaiser , B. J. , Olmsted , R. A. , Kopta , L. A. , Swaney , S. M. , Poppe , S. M. , Morris , J. , Tarpley , W. G. and Thomas , R. C. 1998 . Pyrimidine thioethers: A novel class of HIV‐1 reverse transcriptase inhibitors with activity against BHAP‐resistant HIV . J. Med. Chem. , 41 : 3793 – 3803 .
  • Campaigne , E. , Ellis , R. L. , Bradford , M. and Ho , J. 1996 . Synthesis of some ureidodihydrofurans and related pyrimidones as potential antimalarials . J. Med. Chem. , 12 : 339 – 342 .
  • Singh , K. , Singh , S. and Mahajan , A. 2005 . Metalation of Biginelli compounds: A general unprecedented route to C‐6 functionalized 4‐aryl‐3,4‐dihydropyrimidinones . J. Org. Chem. , 70 : 6114 – 6117 .
  • Petricci , E. , Radi , M. , Corelli , F. and Botta , M. 2003 . Microwave‐enhanced Sonogashira coupling reaction of substituted pyrimidinones and pyrimidine nucleosides . Tetrahedron Lett. , 44 : 9181 – 9184 .
  • Makarov , V. A. , Riabova , O. B. , Granik , V. G. , Dahse , H. M. , Stelzner , A. , Wutzlerc , P. and Schmidtke , M. 2005 . Anti‐coxsackievirus B3 activity of 2‐amino‐3‐nitropyrazolo[1,5‐a]pyrimidines and their analogs . Bioorg. Med. Chem. Lett. , 15 : 37 – 39 .
  • Sharma , P. , Kumar , A. , Rane , N. and Gurram , V. 2005 . Hetero Diels–Alder reaction: A novel strategy to regioselective synthesis of pyrimido[4,5‐d]pyrimidine analogues from Biginelli derivative . Tetrahedron , 61 : 4237 – 4248 .
  • Nobuaki Matsumoto , N. and Takahashi , M. 2005 . Synthesis of pyrrolo[2,3‐d]pyrimidine‐2,4‐diones by sunlight photolysis of N‐(5‐vinyluracil‐6‐yl)sulfilimines . Tetrahedron Lett. , 46 : 5551 – 5554 .
  • Wang , S. , Folkes , A. , Chuckowree , I. , Cockcroft , X. , Sohal , S. , Miller , W. , Milton , S. J. , Wren , S. P. , Vicker , N. , Depledge , P. , Scott , J. , Smith , L. , Jones , H. , Mistry , P. , Faint , R. F. , Thompson , D. and Cocks , S. 2004 . Studies on pyrrolopyrimidines as selective inhibitors of multidrug‐resistance‐associated protein in multidrug resistance . J. Med. Chem. , 47 : 1329 – 1338 .
  • Agarwal , A. , Goyal , N. , Chauhana , P. M.S. and Gupta , S. 2005 . Dihydropyrido[2,3‐d]pyrimidines as a new class of antileishmanial agents . Bioorg. Med. Chem. , 13 : 6678 – 6684 .
  • Pontillo , J. and Chen , C. 2005 . Efficient synthesis of bicyclic oxazolino‐ and thiazolino[3,2‐c]pyrimidine‐5,7‐diones and its application to the synthesis of GnRH antagonists . Bioorg. Med. Chem. Lett. , 15 : 1407 – 1411 .
  • Alberti , M. J. , Auten , E. P. , Lackey , K. E. , McDonald , O. B. , Wood , E. R. , Preugschat , F. , Cutler , G. J. , Kane‐Carson , L. , Liu , W. and Jung , D. K. 2005 . Discovery and in vitro evaluation of potent kinase inhibitors: Pyrido[10,20:1,5]pyrazolo[3,4‐d]pyrimidines . Bioorg. Med. Chem. Lett. , 15 : 3778 – 3781 .
  • Baraldi , P. G. , El‐Kashef , H. , Farghaly , A. R. , Vanellec , P. and Fruttaroloa , F. 2004 . Synthesis of new pyrazolo[4,3‐e]‐1,2,4‐triazolo[1,5‐c]pyrimidines and related heterocycles . Tetrahedron , 60 : 5093 – 5104 .
  • Naya , S. I. , Miyagawa , M. and Nitta , M. 2005 . Novel photo‐induced oxidative cyclization of 1,3‐dimethyl‐5‐(1‐arylmethylidene)pyrimidine‐2,4,6(1,3,5H)‐triones: Synthesis and properties of areno[5,6]pyrano[2,3‐d]pyrimidine‐2,4(1,3H)‐dionylium ions and their photo‐induced autorecycling oxidizing reaction toward some amines . Tetrahedron , 61 : 4919 – 4930 .
  • Waelchli , R. , Bollbuck , B. , Bruns , C. , Buhl , T. , Eder , J. , Feifel , R. , Hersperger , R. , Janser , P. , Revesz , L. , Zerwes , H. and Schlapbach , A. 2006 . Design and preparation of 2‐benzamido‐pyrimidines as inhibitors of IKK . Bioorg. Med. Chem. Lett. , 16 : 108 – 112 .
  • Zhi , C. , Long , Z. Y. , Gambino , J. , Xu , W. C. , Brown , N. C. , Barnes , M. , Butler , M. , LaMarr , W. and Wright , G. E. 2003 . Synthesis of substituted 6‐anilinouracils and their inhibition of DNA, polymerase IIIC and gram‐positive bacterial growth . J. Med. Chem. , 46 : 2731 – 2739 .
  • Devi , I. and Bhuyan , P. J. 2005 . An expedient method for the synthesis of 6‐substituted uracils under microwave irradiation in a solvent‐free medium . Tetrahedron Lett. , 46 : 5727 – 5729 .
  • Waynebills , C. W. , Gebura , S. E. , Meek , J. S. and Sweeti , O. J. 1962 . New synthesis of uric acid and dimethyluric acid . J. Org. Chem. , 27 : 4633 – 4635 .
  • Muller , C. E. , Shi , D. , Manning , M. and Daly , J. W. 1993 . Synthesis of paraxanthine analogs (1,7‐disubstituted xanthines) and other xanthines unsubstituted at the 3‐position: Structure–activity relationships at adenosine receptors . J. Med. Chem. , 36 : 3341 – 3349 .
  • Lee , Y. , Kim , S. Y. , Lee , J. Y. , Yu , C. M. , Lee , D. H. and Gong , Y. D. 2004 . Solution‐phase parallel synthesis of new 2H‐pyrimido‐[4,5‐e][1,2,4]triazin‐3‐ylidenecyanamides . Tetrahedron Lett. , 45 : 9319 – 9322 .
  • Langen , P. , Etzold , G. , Bärwolff , D. and Preussel , B. 1967 . Inhibition of thymidine phosphorylase by 6‐aminothymine and derivatives of 6‐aminouracil . Biochem. Pharmacol. , 16 : 1833 – 1837 .
  • Ali , A. , Taylor , G. E. , Ellsworth , K. , Harris , G. , Painter , R. , Silver , L. L. and Young , K. 2003 . Novel pyrazolo[3,4‐d]pyrimidine‐based inhibitors of Staphlococcus aureus DNA polymerase III: Design, synthesis, and biological evaluation . J. Med. Chem. , 46 : 1824 – 1830 .
  • Baraldi , P. G. , Preti , D. , Tabrizi , M. A. , Fruttarolo , F. , Romagnoli , R. , Zaid , N. A. , Moorman , A. R. , Merighi , S. , Varani , K. and Borea , P. A. 2005 . New pyrrolo[2,1‐f]purine‐2,4‐dione and imidazo[2,1‐f]purine‐2,4‐dione derivatives as potent and selective human A3 adenosine receptor antagonists . J. Med. Chem. , 48 : 4697 – 4701 .
  • Devi , I. , Kumar , B. S.D. and Bhuyana , P. J. 2003 . A novel three‐component one‐pot synthesis of pyrano[2,3‐d]pyrimidines and pyrido[2,3‐d]pyrimidines using microwave heating in the solid state . Tetrahedron Lett. , 44 : 8307 – 8310 .
  • Bagley , M. C. and Singh , N. 2002 . Microwave‐assisted synthesis of 5‐deaza‐5,8‐dihydropterins . Synlett , : 1718 – 1720 .
  • Agarwal , A. and Chauhan , P. M. S. 2005 . Solid supported synthesis of structurally diverse dihydropyrido[2,3‐d]pyrimidines using microwave irradiation . Tetrahedron Lett. , 46 : 1345 – 1348 .
  • Azizian , J. , Mohammadizadeh , M. R. , Mohammadi , A. A. , Karimi , A. R. and Teimouri , F. A novel one‐pot procedure for preparation of some new condensed pyrido[2,3‐d]pyrimidine(1H,3H)‐2,4‐diones . Heteroatom. Chem. , (in press)
  • Pourashraf , M. , Delair , P. , Rasmaissen , M. O. and Greene , A. E. 2000 . Highly enantioselective approach to indolizidines: Preparation of (+)‐(1S,8aS)‐1‐hydroxyindolizidine and (−)‐slaframine . J. Org. Chem. , 65 : 6966 – 6972 .
  • Lidstrom , P. , Tierney , J. , Wathey , B. and Westman , J. 2001 . Microwave assisted organic synthesis—a review . Tetrahedron , 57 : 9225 – 9283 .
  • Bougrin , K. , Loupy , A. and Soufiaoui , M. J. 2005 . Microwave‐assisted solvent‐free heterocyclic synthesis . J. Photochem. Photobiol. C , 6 : 139 – 167 .
  • Azizian , J. , Karimi , A. R. , Kazemizadeh , Z. , Mohammadi , A. A. and Mohammadizadeh , M. R. 2005 . A synthetic route to 11‐(1H‐pyrrol‐1‐yl)‐11H‐indeno[1,2‐b]quinoxaline derivatives exploiting a three‐component coupling strategy under microwave irradiation . Tetrahedron Lett. , 46 : 6155 – 6157 .
  • Azizian , J. , Karimi , A. R. and Mohammadi , A. A. 2003 . An efficient one‐pot procedure for preparation of 2,4(1H,3H)‐quinazolinediones and 2‐thioxoquinazolinone derivatives under microwave irradiation . Synth. Commun. , 33 : 415 – 420 .
  • Azizian , J. , Karimi , A. R. , Kazemizadeh , Z. , Mohammadi , A. A. and Mohammadizadeh , M. R. 2005 . A novel one‐pot synthesis of some new interesting pyrrole derivatives . J. Org. Chem. , 70 : 1471 – 1473 .

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