ZrCl4-Catalyzed Michael Reaction of 1,3-Dicarbonyls and Enones under Solvent-Free Conditions

G. Smitha; Sujatha Patnaik; Ch. Sanjeeva Reddy

doi:10.1055/s-2005-861837

SHORTPAPER

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, India
e-Mail: chsrkuc@yahoo.co.in;

Abstract

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

<A NAME="RZ18804SS-1A">1a</A> Lewis RJSR. Dangerous Properties of Industrial Materials 7th ed., Vol. 3: Van Nostrand Reinhold; New York: 1989.

<A NAME="RZ18804SS-1B">1b</A> Riley JP. Chester R. Introduction to Marine Chemistry Academic Press; New York: 1971.

<A NAME="RZ18804SS-1C">1c</A> Farnworth F. Jones SL. McAlpine I. Speciality Inorganic Chemicals, Special Publication No. 40 Royal Society of Chemistry; London: 1980.

<A NAME="RZ18804SS-1D">1d</A> Bora U. Synlett 2003, 1073

<A NAME="RZ18804SS-2">2</A> Heine HW. Cottle DL. van Mater HL. J. Am. Chem. Soc. 1946, 68: 524

<A NAME="RZ18804SS-3A">3a</A> Poll T. Helmchen G. Bauer B. Tetrahedron Lett. 1984, 25: 2191

<A NAME="RZ18804SS-3B">3b</A> Evans DA. Chapman KT. Bisaha J. J. Am. Chem. Soc. 1988, 110: 1238

<A NAME="RZ18804SS-4">4</A> Reddy CV. Mahesh M. Raju PVK. Babu TR. Reddy VVN. Tetrahedron Lett. 2002, 43: 2657

<A NAME="RZ18804SS-5A">5a</A> Firouzabadi H. Iranpoor N. Karimi B. Synlett 1999, 319

<A NAME="RZ18804SS-5B">5b</A> Firouzabadi H. Iranpoor N. Karimi B. Synlett 1999, 321

<A NAME="RZ18804SS-6A">6a</A> Chakraborti AK. Kondaskar A. Tetrahedron Lett. 2003, 44: 8315

<A NAME="RZ18804SS-6B">6b</A> Swamy RN. Goud TV. Reddy SM. Krishnaiah P. Venkateshwarlu Y. Synth. Commun. 2004, 34: 727

<A NAME="RZ18804SS-7A">7a</A> Babu KS. Raju BC. Srinivas PV. Tetrahedron Lett. 2003, 44: 2525

<A NAME="RZ18804SS-7B">7b</A> Sharma GVM. Reddy CG. Krishna PR. Synlett 2003, 1728

<A NAME="RZ18804SS-7C">7c</A> Sharma GVM. Reddy CG. Krishna PR. J. Org. Chem. 2003, 68: 4574

<A NAME="RZ18804SS-7D">7d</A> Sharma GVM. Srinivas B. Krishna PR. Tetrahedron Lett. 2003, 44: 4689

<A NAME="RZ18804SS-7E">7e</A> Rezai N. Meybodi FA. Salehi P. Synth. Commun. 2000, 30: 1799

<A NAME="RZ18804SS-8A">8a</A> Sharma GVM. Reddy JJ. Lakshmi PS. Krishna PR. Tetrahedron Lett. 2004, 45: 6963

<A NAME="RZ18804SS-8B">8b</A> Firouzabadi H. Iranpoor N. Jafarpour M. Tetrahedron Lett. 2004, 45: 7451

<A NAME="RZ18804SS-8C">8c</A> Chakraborti AK. Gulhane R. Synlett 2004, 627

<A NAME="RZ18804SS-8D">8d</A> Yadav JS. Reddy BVS. Raj KS. Reddy KB. Prasad AR. Synlett 2001, 2277

<A NAME="RZ18804SS-8E">8e</A> Akiyama T. Yamanaka M. Synlett 1996, 1095

<A NAME="RZ18804SS-9A">9a</A> Smitha G. Reddy ChS. Synth. Commun. 2004, 34: 3997

<A NAME="RZ18804SS-9B">9b</A> Smitha G. Reddy ChS. J. Chem. Res. 2004, 300

<A NAME="RZ18804SS-9C">9c</A> Smitha G. Reddy ChS. Synthesis 2004, 834

<A NAME="RZ18804SS-9D">9d</A> Smitha G. Reddy ChS. Tetrahedron 2003, 59: 9571

<A NAME="RZ18804SS-9E">9e</A> Reddy ChS. Smitha G. Chandrasekhar S. Tetrahedron Lett. 2003, 44: 4693

<A NAME="RZ18804SS-10A">10a</A> Perlmutter P. Tetrahedron Organic Chemistry Series Vol. 9: Pergamon; Oxford: 1992.

<A NAME="RZ18804SS-10B">10b</A> Jung ME. In Comprehensive Organic Synthesis Vol. 4: Trost BM. Fleming I. Pergamon; Oxford: 1991. p.1

<A NAME="RZ18804SS-11">11</A> Bergmann ED. Ginsburg D. Pappo R. Org. React. 1953, 10: 179

<A NAME="RZ18804SS-12A">12a</A> Rele DN. Trivedi GK. J. Sci. Ind. Res. 1993, 52: 13

<A NAME="RZ18804SS-12B">12b</A> Nelson JH. Howells PN. DeLullo GC. Landen GL. Henry RA. J. Org. Chem. 1980, 45: 1246

<A NAME="RZ18804SS-13">13</A> Christoffers J. Eur. J. Org. Chem. 1998, 1259

<A NAME="RZ18804SS-14A">14a</A> Soriente A. Spinella A. Rosa MD. Giordano M. Scettri A. Tetrahedron Lett. 1997, 38: 289

<A NAME="RZ18804SS-14B">14b</A> Van Westrenen J. Roggen RM. Hoefnagel MA. Peters JA. Kieboom APG. Van Bekkum H. Tetrahedron 1990, 46: 5741

<A NAME="RZ18804SS-15">15</A> Antonioletti R. Bonandien F. Monteagudo ES. Scettri A. Tetrahedron Lett. 1991, 32: 5373

<A NAME="RZ18804SS-16">16</A> Boyer J. Corriu RJP. Pers R. Reye C. J. Chem. Soc., Chem. Commun. 1981, 122

<A NAME="RZ18804SS-17">17</A> Soriente A. Arienzo R. Rosa MD. Palombi L. Spinella A. Scettri A. Green Chem. 1999, 157

<A NAME="RZ18804SS-18A">18a</A> Boruah A. Baruah M. Prajapati D. Sandhu JS. Chem. Lett. 1996, 965

<A NAME="RZ18804SS-18B">18b</A> Ranu BC. Bhar S. Tetrahedron Lett. 1992, 48: 1327

<A NAME="RZ18804SS-19A">19a</A> Shimizu K. Miyagi M. Kanno T. Kodama T. Kitayama Y. Tetrahedron Lett. 2003, 44: 7421

<A NAME="RZ18804SS-19B">19b</A> Dell’Anna MM. Gallo V. Mastrorilli P. Nobile CF. Romanazzi G. Suranna GP. Chem. Commun. 2002, 434

<A NAME="RZ18804SS-19C">19c</A> Picquet M. Bruneau C. Dixneuf PH. Tetrahedron 1999, 55: 3937

<A NAME="RZ18804SS-19D">19d</A> Boruah A. Baruah M. Prajapati D. Sandhu JS. Synth. Commun. 1998, 28: 653

<A NAME="RZ18804SS-19E">19e</A> Sreekumar R. Rugmini P. Padmakumar R. Tetrahedron Lett. 1997, 38: 6557

<A NAME="RZ18804SS-20">20</A> Bartoli G. Bosco M. Bellucci MC. Marcantoni E. Sambri L. Torregiani E. Eur. J. Org. Chem. 1999, 617

<A NAME="RZ18804SS-21">21</A> Christoffers J. J. Chem. Soc., Perkin Trans. 1 1997, 3141

<A NAME="RZ18804SS-22">22</A> Yadav JS. Geetha V. Reddy BVS. Synth. Commun. 2002, 32: 3519

<A NAME="RZ18804SS-23">23</A> Bensa D. Rodriguez J. Synth. Commun. 2004, 34: 1515

<A NAME="RZ18804SS-24">24</A> Bensa D. Constantieux T. Rodriguez J. Synthesis 2004, 923

<A NAME="RZ18804SS-25">25</A> Kawabata T. Mizugaki T. Ebitani K. Kaneda K. J. Am. Chem. Soc. 2003, 125: 10486

<A NAME="RZ18804SS-26">26</A> Begue JP. Bonnet-Delpon D. Dogbeavou A. Synth. Commun. 1992, 22: 573