Synthesis, Table of Contents SHORTPAPER © Georg Thieme Verlag Stuttgart · New York ZrCl4-Catalyzed Michael Reaction of 1,3-Dicarbonyls and Enones under Solvent-Free Conditions G. Smitha, Sujatha Patnaik, Ch. Sanjeeva Reddy*Department of Chemistry, Kakatiya University, Warangal-506 009, Indiae-Mail: chsrkuc@yahoo.co.in; Recommend Article Abstract Buy Article All articles of this category Abstract ZrCl4 has been found to catalyze the conjugate addition of 1,3-dicarbonyl compounds with enones. The reaction does not require any solvent and proceeds smoothly at room temperature leading to the corresponding adduct in good yields. Key words zirconium(IV) chloride - Michael reaction - 1,3-dicarbonyls - enones Full Text References References 1a Lewis RJSR. Dangerous Properties of Industrial Materials 7th ed., Vol. 3: Van Nostrand Reinhold; New York: 1989. 1b Riley JP. Chester R. Introduction to Marine Chemistry Academic Press; New York: 1971. 1c Farnworth F. Jones SL. McAlpine I. Speciality Inorganic Chemicals, Special Publication No. 40 Royal Society of Chemistry; London: 1980. 1d Bora U. Synlett 2003, 1073 2 Heine HW. Cottle DL. van Mater HL. J. Am. Chem. Soc. 1946, 68: 524 3a Poll T. Helmchen G. Bauer B. Tetrahedron Lett. 1984, 25: 2191 3b Evans DA. Chapman KT. Bisaha J. J. Am. Chem. Soc. 1988, 110: 1238 4 Reddy CV. Mahesh M. Raju PVK. Babu TR. Reddy VVN. Tetrahedron Lett. 2002, 43: 2657 5a Firouzabadi H. Iranpoor N. Karimi B. Synlett 1999, 319 5b Firouzabadi H. Iranpoor N. Karimi B. Synlett 1999, 321 6a Chakraborti AK. Kondaskar A. Tetrahedron Lett. 2003, 44: 8315 6b Swamy RN. Goud TV. Reddy SM. Krishnaiah P. Venkateshwarlu Y. Synth. Commun. 2004, 34: 727 7a Babu KS. Raju BC. Srinivas PV. Tetrahedron Lett. 2003, 44: 2525 7b Sharma GVM. Reddy CG. Krishna PR. Synlett 2003, 1728 7c Sharma GVM. Reddy CG. Krishna PR. J. Org. Chem. 2003, 68: 4574 7d Sharma GVM. Srinivas B. Krishna PR. Tetrahedron Lett. 2003, 44: 4689 7e Rezai N. Meybodi FA. Salehi P. Synth. Commun. 2000, 30: 1799 8a Sharma GVM. Reddy JJ. Lakshmi PS. Krishna PR. Tetrahedron Lett. 2004, 45: 6963 8b Firouzabadi H. Iranpoor N. Jafarpour M. Tetrahedron Lett. 2004, 45: 7451 8c Chakraborti AK. Gulhane R. Synlett 2004, 627 8d Yadav JS. Reddy BVS. Raj KS. Reddy KB. Prasad AR. Synlett 2001, 2277 8e Akiyama T. Yamanaka M. Synlett 1996, 1095 9a Smitha G. Reddy ChS. Synth. Commun. 2004, 34: 3997 9b Smitha G. Reddy ChS. J. Chem. Res. 2004, 300 9c Smitha G. Reddy ChS. Synthesis 2004, 834 9d Smitha G. Reddy ChS. Tetrahedron 2003, 59: 9571 9e Reddy ChS. Smitha G. Chandrasekhar S. Tetrahedron Lett. 2003, 44: 4693 10a Perlmutter P. Tetrahedron Organic Chemistry Series Vol. 9: Pergamon; Oxford: 1992. 10b Jung ME. In Comprehensive Organic Synthesis Vol. 4: Trost BM. Fleming I. Pergamon; Oxford: 1991. p.1 11 Bergmann ED. Ginsburg D. Pappo R. Org. React. 1953, 10: 179 12a Rele DN. Trivedi GK. J. Sci. Ind. Res. 1993, 52: 13 12b Nelson JH. Howells PN. DeLullo GC. Landen GL. Henry RA. J. Org. Chem. 1980, 45: 1246 13 Christoffers J. Eur. J. Org. Chem. 1998, 1259 14a Soriente A. Spinella A. Rosa MD. Giordano M. Scettri A. Tetrahedron Lett. 1997, 38: 289 14b Van Westrenen J. Roggen RM. Hoefnagel MA. Peters JA. Kieboom APG. Van Bekkum H. Tetrahedron 1990, 46: 5741 15 Antonioletti R. Bonandien F. Monteagudo ES. Scettri A. Tetrahedron Lett. 1991, 32: 5373 16 Boyer J. Corriu RJP. Pers R. Reye C. J. Chem. Soc., Chem. Commun. 1981, 122 17 Soriente A. Arienzo R. Rosa MD. Palombi L. Spinella A. Scettri A. Green Chem. 1999, 157 18a Boruah A. Baruah M. Prajapati D. Sandhu JS. Chem. Lett. 1996, 965 18b Ranu BC. Bhar S. Tetrahedron Lett. 1992, 48: 1327 19a Shimizu K. Miyagi M. Kanno T. Kodama T. Kitayama Y. Tetrahedron Lett. 2003, 44: 7421 19b Dell’Anna MM. Gallo V. Mastrorilli P. Nobile CF. Romanazzi G. Suranna GP. Chem. Commun. 2002, 434 19c Picquet M. Bruneau C. Dixneuf PH. Tetrahedron 1999, 55: 3937 19d Boruah A. Baruah M. Prajapati D. Sandhu JS. Synth. Commun. 1998, 28: 653 19e Sreekumar R. Rugmini P. Padmakumar R. Tetrahedron Lett. 1997, 38: 6557 20 Bartoli G. Bosco M. Bellucci MC. Marcantoni E. Sambri L. Torregiani E. Eur. J. Org. Chem. 1999, 617 21 Christoffers J. J. Chem. Soc., Perkin Trans. 1 1997, 3141 22 Yadav JS. Geetha V. Reddy BVS. Synth. Commun. 2002, 32: 3519 23 Bensa D. Rodriguez J. Synth. Commun. 2004, 34: 1515 24 Bensa D. Constantieux T. Rodriguez J. Synthesis 2004, 923 25 Kawabata T. Mizugaki T. Ebitani K. Kaneda K. J. Am. Chem. Soc. 2003, 125: 10486 26 Begue JP. Bonnet-Delpon D. Dogbeavou A. Synth. Commun. 1992, 22: 573
