General and Green Synthesis of C-6 Sulfonylmethyl 4-Aryl-3,4-dihydropyrimidinones in Water

REFERENCES

• (a) Li , C. J. Organic reactions in aqueous media with a focus on carbon–carbon bond formation . Chem. Rev. 1993 , 93 , 2023 – 2035 ; (b) Li , C. J. Organic reactions in aqueous media with a focus on carbon–carbon bond formations: A decade update . Chem. Rev. 2005 , 105 , 3095 – 3166 .
   Web of Science ®Google Scholar
• Lindeström , U. M. Stereoselective organic reactions in water . Chem. Rev. 2002 , 102 , 2751 – 2772 .
   Google Scholar
• (a) Biginelli , P. Aldehyde–urea derivatives of aceto- and oxaloacetic acids . Gazz. Chim. Ital. 1893 , 23 , 360 – 413 ; (b) Kappe , C. O. One hundred years of the Biginelli dihydropyrimidine synthesis . Tetrahedron 1993 , 49 , 6937 – 6963 ; (c) Kappe , C. O. Recent advances in the Biginelli dihydropyrimidine synthesis: New tricks from an old dog . Acc. Chem. Res. 2000 , 33 , 879 – 888 , and references cited therein .
   Google Scholar
• Kappe , C. O. Biologically active dihydropyrimidones of the Biginelli-type—A literature survey . Eur. J. Med. Chem. 2000 , 35 , 1043 – 1052 .
   PubMed Web of Science ®Google Scholar
• (a) Atwal , K. S. ; Rovnyak , G. C. ; Schwartz , J. ; Moreland , S. ; Hedberg , A. ; Gougoutas , J. Z. ; Malley , M. F. ; Floyd , D. M. Dihydropyrimidine calcium channel blockers: 2-Heterosubstituted 4-aryl-1,4-dihydro-6-methyl-5-pyrimidinecarboxylic acid esters as potent mimics of dihydropyridines . J. Med. Chem. 1990 , 33 , 1510 – 1515 ; (b) Rovnyak , G. C. ; Kimball , S. D. ; Beyer , B. ; Gucinotta , G. ; DiMarco , J. D. ; Gougoutas , J. C. ; Hedberg , A. ; Malley , M. ; McCarthy , J. P. ; Zhang , R. ; Moreland , S. Calcium entry blockers and activators: Conformational and structural determinants of dihydropyrimidine calcium channel modulators . J. Med. Chem. 1995 , 38 , 119 – 129 .
   PubMed Web of Science ®Google Scholar
• (a) Lagu , B. ; Tian , D. ; Chiu , G. ; Nagarathnam , D. ; Fang , J. ; Shen , Q. ; Forray , C. ; Ransom , R. ; Chang , R. S. L. ; Vyas , K. P. ; Zhang , K. ; Gluchowski , C. Synthesis and evaluation of furo[3,4-d]pyrimidinones as selective alpha(1a)-adrenergic receptor antagonists . Bioorg. Med. Chem. Lett. 2000 , 10 , 175 – 178 ; (b) Barrow , J. C. ; Nantermet , P. G. ; Selnick , H. G. ; Glass , K. L. ; Rittle , K. E. ; Gilbert , K. F. ; Steele , T. G. ; Homnick , C. F. ; Freidinger , T. W. ; Ransom , R. W. ; Kling , P. ; Reiss , D. ; Broten , T. P. ; Schorn , T. W. ; Chang , R. S. L. ; O'Malley , S. S. ; Olah , T. V. ; Ellis , J. D. ; Barrish , A. ; Kassahun , K. ; Leppert , P. ; Nagarathnam , D. ; Forray , C. In vitro and in vivo evaluation of dihydropyrimidinone C-5 amides as potent and selective α1A receptor antagonists for the treatment of benign prostatic hyperplasia . J. Med. Chem. 2000 , 43 , 2703 – 2718 .
   PubMedGoogle Scholar
• (a) Kappe , C. O. Synthesis and reactions of Biginelli compounds 3: Unexpected formation of nitriles from reactions of 6-(dibromomethyl)-1,2,3,4-tetrahydro-2-oxo-5-pyrimidinecarboxylates with sodium-azide . Liebigs Ann. Chem. 1990 , 505 – 507 ; (b) Khanetskyy , B. ; Dallinger , D. ; Kappe , C. O. Combining Biginelli multicomponent and click chemistry: Generation of 6-(1,2,3-triazol-1-yl)-dihydropyrimidone libraries . J. Comb. Chem. 2004 , 6 , 884 – 892 .
   Google Scholar
• Pérez , R. ; Beryozkina , T. ; Zbruyev , O. I. ; Haas , W. ; Kappe , C. O. Traceless solid-phase synthesis of bicyclic dihydropyrimidones using multidirectional cyclization cleavage . J. Comb. Chem. 2002 , 4 , 501 – 510 , and references cited herein .
   PubMed Web of Science ®Google Scholar
• Singh , K. ; Singh , S. ; Mahajan , A. Metalation of Biginelli compounds: A general unprecedented route to C-6 functionalized 4-aryl-3,4-dihydropyrimidinones. J. Org. Chem. 2005, 70, 6114–6117.
   PubMedGoogle Scholar
• (a) Wang , X. C. ; Quan , Z. J. ; Zhang , Z. Michael additions of dihydropyrimidines and 2-amino-1,3,4-thiadiazoles to α,β-ethylenic compounds: Using polyethylene glycols as a green reaction media . Tetrahedron 2007 , 63 , 8227 – 8233 ; (b) Wang , X. C. ; Quan , Z. J. ; Wang , J. K. ; Zhang , Z. ; Wang , M. G. A practical and green approach towards synthesis of N 3 substituted dihydropyrimidinones: Using aza-Michael addition reaction catalyzed by KF/Al2O3 . Bioorg. Med. Chem. Lett. 2006 , 16 , 4592 – 4595 ; (c) Wang , X. C. ; Quan , Z. J. ; Zhang , Z. An environmentally benign access to dimethylated 3,4-dihydropyrimidines using dimethyl carbonate as methylating agent under microwave . Chin. J. Chem. 2008 , 26 , 368 – 372 ; (d) Quan , Z. J. ; Zhang , Z. ; Wang , J. K. ; Wang , X. C. ; Liu , Y. J. ; Ji , P. Y. Efficient synthesis of 5H-thiazolo[3,2-a]pyrimidines from reactions of 3,4-dihydropyrimidine-thiones with α-bromoacetone in aqueous media . Heteroatom Chem. 2008 , 19 , 149 – 153 .
   Web of Science ®Google Scholar
• (a) Stephens , C. E. ; Felder , T. M. ; Sowell , J. W. ; Andrei , G. ; Balzarini , J. ; Snoeck , R. ; De Clercq , E. Synthesis and antiviral/antitumor evaluation of 2-amino- and 2-carboxamido-3-arylsulfonythiophenes and related compounds as a new class of diarylsulfones . Bioorg. Med. Chem. 2001 , 9 , 1123 – 1132 ; (b) Garuti , L. ; Roberti , M. ; De Clercq , E. Synthesis and antiviral/antiproliferative activity of some N-sulphonylbenzimidazoles . Bioorg. Med. Chem. Lett. 2002 , 12 , 2707 – 2710 ; (c) Gellis , A. ; Boufatah , N. ; Vanelle , P. Rapid microwave-promoted synthesis of new sulfonylmethylbenzothiazoles in water . Green Chem. 2006 , 8 , 483 – 487 .
   PubMed Web of Science ®Google Scholar
• O'Connel , J. F. ; Rapoport , H. 1-Benzenesulfonyl- and 1-p-toluenesulfonyl-3-methylimidazolium triflates: Efficient reagents for the preparation of arylsulfonamides and arylsulfonates . J. Org. Chem. 1992 , 57 , 4775 – 4777 .
   Web of Science ®Google Scholar
• (a) Zigeuner , G. ; Knopp , C. ; Blaschke , H. Tetrahydro-6-methyl-2-oxopyrimidin-5-carboxylic and tetrahydro-6-phenyl-2-oxopyrimidin-5-carboxylic acids and deriatives, 48: Heterocyclic compounds . Monatsh. Chem. 1976 , 107 , 587 – 603 ; (b) George , T. ; Tahilramani , R. ; Metha , D. V. Condensed heterocycles from 5-ethoxycarbonyl-6-methyltetrahydropyrimidin-2-ones . Synthesis 1975 , 405 – 407 ; (c) Ashby , J. ; Griffiths , D. Some base-catalysed ring expansion and ring expansion–ring contraction reactions of ethyl 4-chloromethyl-1,2,3,4-tetrahydro-6-methyl-2-oxopyrimidine-5-carboxylate . J. Chem. Soc., Perkin Trans. 1 1975 , 657 – 662 ; (d) Zigeuner , G. ; Knopp , C. 3,4,6,7-Tetrahydro-5H-pyryolo[3,4-d]pyrimidin-2(1H)-5-dione, 22: Heterocyclic compounds . Monatsh. Chem. 1970 , 101 , 1541 – 1546 .
   Google Scholar
• Clark , J. H. (Ed.) Chemistry of Waste Minimization ; Chapman and Hall : London , 1995 .
   Google Scholar
• (a) Chaudhuri , M. K. ; Khan , A. T. ; Patel , B. K. ; Dey , D. ; Kharmawophlang , W. ; Lakshmiprabha , T. R. ; Mandal , G. C. An environmentally benign synthesis of organic ammonium tribromides (OATB) and bromination of selected organic substrates by tetrabutylammonium tribromide (TBATB) . Tetrahedron Lett. 1998 , 39 , 8163 – 8166 ; (b) Bose , G. ; Barua , P. M. B. ; Chaudhuri , M. K. ; Kalita , D. ; Khan , A. T. A convenient and useful method of preparation of alpha-bromo enones from the corresponding enones using organic ammonium tribromide (OATB) . Chem. Lett. 2001 , 290 – 291 ; (c) Mondal , E. ; Sahu , P. R. ; Bose , G. ; Khan , A. T. A useful and convenient synthetic protocol for interconversion of carbonyl compounds to the corresponding 1,3-oxathiolanes and vice versa employing organic ammonium tribromide (OATB) . Tetrahedron Lett. 2002 , 43 , 2843 – 2846 .
   Web of Science ®Google Scholar
• Wang , X. C. ; Quan , Z. J. ; Wang , F. ; Wang , M. G. ; Zhang , Z. ; Li , Z. PEG-SO3H as catalyst for 3,4-dihydropyrimidones via Biginelli reaction under microwave and solvent-free conditions. Synth. Commun. 2006, 36, 451–456.
   Web of Science ®Google Scholar