Synthesis, Inhaltsverzeichnis PAPER © Georg Thieme Verlag Stuttgart ˙ New York Adducts of Diketene, Alcohols, and Aldehydes: Useful Building Blocks for 3,4-Dihydropyrimidinones and 1,4-Dihydropyridines Abdolali Alizadeh*, Sadegh RostamniaDepartment of Chemistry, Tarbiat Modares University, P.O. Box 14115-175, Tehran, IranFax: +98(21)88006544; e-Mail: abdol_alizad@yahoo.com; e-Mail: aalizadeh@modares.ac.ir; Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract A novel, one-pot, solvent-free synthesis of 3,4-dihydropyrimidin-2-(1H)-one and 1,4-dihydropyridines derivatives via a four-component cyclocondensation reaction of diketene, alcohol, and aldehyde with urea or ammonium acetate is presented. Key words dihydropyridines - dihydropyrimidines - diketene - multicomponent reaction - neat condition Volltext Referenzen References 1a Atwal KS. Swanson BN. Unger SE. Floyd DM. Moreland S. Hedberg A. Reilly BC. J. Med. Chem. 1991, 34: 806 1b Kappe CO. Fabian WMF. Tetrahedron 1997, 53: 2803 1c Singh K. Singh J. Deb PK. Singh H. Tetrahedron 1999, 55: 12873 1d Fu NY. Yuan YF. Cao Z. Wang SW. Wang JT. Peppe C. Tetrahedron 2002, 58: 4801 1e Kappe CO. Eur. J. Med. Chem. 2000, 35: 1043 1f Byk G. Gettlieb HE. Herscovici J. Mirkin F. J. Comb. Chem. 2000, 2: 732 1g Mokrosz JL. Paluchowska MH. Szneler E. Drozdz B. Arch. Pharm. (Weinheim, Ger.) 1989, 322: 231 1h Abelman MM. Smith SC. James DR. Tetrahedron Lett. 2003, 44: 4559 2a Janis RA. Triggle DJ. J. Med. Chem. 1983, 26: 775 2b Godfraid T. Miller R. Wibo M. Pharmocol. Rev. 1986, 38: 321 2c Gaudio AC. Korolkovas A. Takahata Y. J. Pharm. Sci. 1994, 83: 1110 2d Klusa V. Drugs Future 1995, 20: 135 3a Chen XH. Xu XY. Liu H. Cun LF. Gong LZ. J. Org. Chem. 2000, 65: 3864 3b Bose DS. Fatima L. Mereyala HB. J. Org. Chem. 2003, 68: 587 3c Hassani Z. Islami MR. Kalantari M. Bioorg. Med. Chem. Lett. 2006, 16: 4479 3d Zumpe FL. Flüb M. Schmitz K. Lender A. Tetrahedron Lett. 2007, 48: 1421 3e Kalita HR. Phukan P. Catal. Commun. 2007, 8: 179 3f Hu EH. Sidler DR. Dolling UH. J. Org. Chem. 1998, 63: 3454 3g Sabitha G. Kumar Reddy GSK. Reddy CS. Yadav JS. Synlett 2003, 858 3h Shaabani A. Bazgir A. Teimouri F. Tetrahedron Lett. 2003, 44: 857 3i Lu J. Ma H. Synlett 2000, 63 3j Reddy YT. Rajitha B. Reddy PN. Kumar BS. Rao VP. Synth. Commun. 2004, 34: 3821 3k Suzuki I. Suzumura Y. Takeda K. Tetrahedron Lett. 2006, 47: 7861 4a Hantzsch A. Justus Liebigs Ann. Chem. 1882, 215: 1 4b Filipan-Litvić M. Litvić M. Cepanec I. Vinković V. Molecules 2007, 12: 2546 4c Alarcon C.-L. Vergara LJN. Squella JA. Electrochim. Acta 2003, 48: 2505 4d Debache A. Boulcina R. Belfaitah A. Rhouati S. Carbonib B. Synlett 2008, 509 4e Osnaya R. Arroyo GA. Parada L. Delgado F. Trujillo J. Salmón R. Miranda M. ARKIVOC 2003, (xi): 112 4f Minga L. Si GW. Rong WL. Feng LY. Zheng YH. J. Mol. Catal. A: Chem. 2006, 258: 133 4g Loev B. Goodman MM. Snader KM. Tedeschi R. Macko E. J. Med. Chem. 1974, 17: 956 4h Simon C. Constantieux T. Rodriguez J. Eur. J. Org. Chem. 2004, 4957 4i Eisner D. Kuthan UJ. Chem. Rev. 1972, 72: 1 4j Sharma GVM. Reddy KL. Lakshmi PS. Krishna PR. Synthesis 2006, 55 4k Zolfigol MA. Salehi P. Safaiee M. Lett. Org. Chem. 2006, 3: 153 4l Zolfigol MA. Safaiee M. Synlett 2004, 827 4m Moghadam M. Nasr M. Tangestaninejad S. Mirkhani V. Bioorg. Med. Chem. Lett. 2006, 16: 2026 4n Lavilla R. J. Chem. Soc., Perkin Trans. 1 2002, 1141 5 Chiba T. Sato H. Kato T. Heterocycles 1984, 22: 493 6a Alizadeh A. Zohreh N. Rostamnia S. Tetrahedron 2007, 63: 8083 6b Alizadeh A. Zohreh N. Zhu LG. Tetrahedron 2009, 65: 2684 6c Alizadeh A. Zohreh N. Zhu L.-G. Synthesis 2009, 464 6d Alizadeh A. Babaki M. Zohreh N. Synthesis 2008, 3295 6e Alizadeh A. Zohreh N. Zhu LG. Synthesis 2008, 2073 6f Alizadeh A. Hosseinpour R. Rostamnia S. Synthesis 2008, 3742 7a Hyatt JA. J. Org. Chem. 1984, 49: 5102 7b Sato M. Kanuma N. Kato T. Chem. Pharm. Bull. 1982, 30: 4359 7c Sato M. Kanuma N. Kato T. Chem. Pharm. Bull. 1982, 30: 1315 7d Baldwin SW. Wilkinson JM. J. Am. Chem. Soc. 1980, 102: 3634 7e Boeckman RK. Thomas AJ. J. Org. Chem. 1982, 47: 2823 7f Jager G. Chem. Ber. 1972, 105: 137 7g Kato T. Kubota Y. Yakugaku Zasshi 1967, 87: 1212 7h Kato T. Kubota Y. Yakugaku Zasshi 1969, 89: 1477
