Adducts of Diketene, Alcohols,
and Aldehydes: Useful Building Blocks for 3,4-Dihydropyrimidinones
and 1,4-Dihydropyridines

Abdolali Alizadeh; Sadegh Rostamnia

doi:10.1055/s-0030-1258291

PAPER

Adducts of Diketene, Alcohols, and Aldehydes: Useful Building Blocks for 3,4-Dihydropyrimidinones and 1,4-Dihydropyridines

Abdolali Alizadeh*, Sadegh Rostamnia
Department of Chemistry, Tarbiat Modares University, P.O. Box 14115-175, Tehran, Iran
Fax: +98(21)88006544; e-Mail: abdol_alizad@yahoo.com; e-Mail: aalizadeh@modares.ac.ir;

Abstract

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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

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References

<A NAME="RZ21010SS-1A">1a</A> Atwal KS. Swanson BN. Unger SE. Floyd DM. Moreland S. Hedberg A. Reilly BC. J. Med. Chem. 1991, 34: 806

<A NAME="RZ21010SS-1B">1b</A> Kappe CO. Fabian WMF. Tetrahedron 1997, 53: 2803

<A NAME="RZ21010SS-1C">1c</A> Singh K. Singh J. Deb PK. Singh H. Tetrahedron 1999, 55: 12873

<A NAME="RZ21010SS-1D">1d</A> Fu NY. Yuan YF. Cao Z. Wang SW. Wang JT. Peppe C. Tetrahedron 2002, 58: 4801

<A NAME="RZ21010SS-1E">1e</A> Kappe CO. Eur. J. Med. Chem. 2000, 35: 1043

<A NAME="RZ21010SS-1F">1f</A> Byk G. Gettlieb HE. Herscovici J. Mirkin F. J. Comb. Chem. 2000, 2: 732

<A NAME="RZ21010SS-1G">1g</A> Mokrosz JL. Paluchowska MH. Szneler E. Drozdz B. Arch. Pharm. (Weinheim, Ger.) 1989, 322: 231

<A NAME="RZ21010SS-1H">1h</A> Abelman MM. Smith SC. James DR. Tetrahedron Lett. 2003, 44: 4559

<A NAME="RZ21010SS-2A">2a</A> Janis RA. Triggle DJ. J. Med. Chem. 1983, 26: 775

<A NAME="RZ21010SS-2B">2b</A> Godfraid T. Miller R. Wibo M. Pharmocol. Rev. 1986, 38: 321

<A NAME="RZ21010SS-2C">2c</A> Gaudio AC. Korolkovas A. Takahata Y. J. Pharm. Sci. 1994, 83: 1110

<A NAME="RZ21010SS-2D">2d</A> Klusa V. Drugs Future 1995, 20: 135

<A NAME="RZ21010SS-3A">3a</A> Chen XH. Xu XY. Liu H. Cun LF. Gong LZ. J. Org. Chem. 2000, 65: 3864

<A NAME="RZ21010SS-3B">3b</A> Bose DS. Fatima L. Mereyala HB. J. Org. Chem. 2003, 68: 587

<A NAME="RZ21010SS-3C">3c</A> Hassani Z. Islami MR. Kalantari M. Bioorg. Med. Chem. Lett. 2006, 16: 4479

<A NAME="RZ21010SS-3D">3d</A> Zumpe FL. Flüb M. Schmitz K. Lender A. Tetrahedron Lett. 2007, 48: 1421

<A NAME="RZ21010SS-3E">3e</A> Kalita HR. Phukan P. Catal. Commun. 2007, 8: 179

<A NAME="RZ21010SS-3F">3f</A> Hu EH. Sidler DR. Dolling UH. J. Org. Chem. 1998, 63: 3454

<A NAME="RZ21010SS-3G">3g</A> Sabitha G. Kumar Reddy GSK. Reddy CS. Yadav JS. Synlett 2003, 858

<A NAME="RZ21010SS-3H">3h</A> Shaabani A. Bazgir A. Teimouri F. Tetrahedron Lett. 2003, 44: 857

<A NAME="RZ21010SS-3I">3i</A> Lu J. Ma H. Synlett 2000, 63

<A NAME="RZ21010SS-3J">3j</A> Reddy YT. Rajitha B. Reddy PN. Kumar BS. Rao VP. Synth. Commun. 2004, 34: 3821

<A NAME="RZ21010SS-3K">3k</A> Suzuki I. Suzumura Y. Takeda K. Tetrahedron Lett. 2006, 47: 7861

<A NAME="RZ21010SS-4A">4a</A> Hantzsch A. Justus Liebigs Ann. Chem. 1882, 215: 1

<A NAME="RZ21010SS-4B">4b</A> Filipan-Litvić M. Litvić M. Cepanec I. Vinković V. Molecules 2007, 12: 2546

<A NAME="RZ21010SS-4C">4c</A> Alarcon C.-L. Vergara LJN. Squella JA. Electrochim. Acta 2003, 48: 2505

<A NAME="RZ21010SS-4D">4d</A> Debache A. Boulcina R. Belfaitah A. Rhouati S. Carbonib B. Synlett 2008, 509

<A NAME="RZ21010SS-4E">4e</A> Osnaya R. Arroyo GA. Parada L. Delgado F. Trujillo J. Salmón R. Miranda M. ARKIVOC 2003, (xi): 112

<A NAME="RZ21010SS-4F">4f</A> Minga L. Si GW. Rong WL. Feng LY. Zheng YH. J. Mol. Catal. A: Chem. 2006, 258: 133

<A NAME="RZ21010SS-4G">4g</A> Loev B. Goodman MM. Snader KM. Tedeschi R. Macko E. J. Med. Chem. 1974, 17: 956

<A NAME="RZ21010SS-4H">4h</A> Simon C. Constantieux T. Rodriguez J. Eur. J. Org. Chem. 2004, 4957

<A NAME="RZ21010SS-4I">4i</A> Eisner D. Kuthan UJ. Chem. Rev. 1972, 72: 1

<A NAME="RZ21010SS-4J">4j</A> Sharma GVM. Reddy KL. Lakshmi PS. Krishna PR. Synthesis 2006, 55

<A NAME="RZ21010SS-4K">4k</A> Zolfigol MA. Salehi P. Safaiee M. Lett. Org. Chem. 2006, 3: 153

<A NAME="RZ21010SS-4L">4l</A> Zolfigol MA. Safaiee M. Synlett 2004, 827

<A NAME="RZ21010SS-4M">4m</A> Moghadam M. Nasr M. Tangestaninejad S. Mirkhani V. Bioorg. Med. Chem. Lett. 2006, 16: 2026

<A NAME="RZ21010SS-4N">4n</A> Lavilla R. J. Chem. Soc., Perkin Trans. 1 2002, 1141

<A NAME="RZ21010SS-5">5</A> Chiba T. Sato H. Kato T. Heterocycles 1984, 22: 493

<A NAME="RZ21010SS-6A">6a</A> Alizadeh A. Zohreh N. Rostamnia S. Tetrahedron 2007, 63: 8083

<A NAME="RZ21010SS-6B">6b</A> Alizadeh A. Zohreh N. Zhu LG. Tetrahedron 2009, 65: 2684

<A NAME="RZ21010SS-6C">6c</A> Alizadeh A. Zohreh N. Zhu L.-G. Synthesis 2009, 464

<A NAME="RZ21010SS-6D">6d</A> Alizadeh A. Babaki M. Zohreh N. Synthesis 2008, 3295

<A NAME="RZ21010SS-6E">6e</A> Alizadeh A. Zohreh N. Zhu LG. Synthesis 2008, 2073

<A NAME="RZ21010SS-6F">6f</A> Alizadeh A. Hosseinpour R. Rostamnia S. Synthesis 2008, 3742

<A NAME="RZ21010SS-7A">7a</A> Hyatt JA. J. Org. Chem. 1984, 49: 5102

<A NAME="RZ21010SS-7B">7b</A> Sato M. Kanuma N. Kato T. Chem. Pharm. Bull. 1982, 30: 4359

<A NAME="RZ21010SS-7C">7c</A> Sato M. Kanuma N. Kato T. Chem. Pharm. Bull. 1982, 30: 1315

<A NAME="RZ21010SS-7D">7d</A> Baldwin SW. Wilkinson JM. J. Am. Chem. Soc. 1980, 102: 3634

<A NAME="RZ21010SS-7E">7e</A> Boeckman RK. Thomas AJ. J. Org. Chem. 1982, 47: 2823

<A NAME="RZ21010SS-7F">7f</A> Jager G. Chem. Ber. 1972, 105: 137

<A NAME="RZ21010SS-7G">7g</A> Kato T. Kubota Y. Yakugaku Zasshi 1967, 87: 1212

<A NAME="RZ21010SS-7H">7h</A> Kato T. Kubota Y. Yakugaku Zasshi 1969, 89: 1477