Reaction of a Trifluoromethylated
N-Monosubstituted Hydrazone with α,β-Ethenyl
Ketones: A Novel Synthesis of Substituted Pyrazolidines and Pyrazolines

Haibo Xie; Jiangtao Zhu; Zixian Chen; Shan Li; Yongming Wu

doi:10.1055/s-0030-1260127

PAPER

Reaction of a Trifluoromethylated N-Monosubstituted Hydrazone with α,β-Ethenyl Ketones: A Novel Synthesis of Substituted Pyrazolidines and Pyrazolines

Haibo Xie, Jiangtao Zhu, Zixian Chen, Shan Li, Yongming Wu*
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China
Fax: +86(21)54925192; e-Mail: ymwu@sioc.ac.cn;

Abstract

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Abstract

We hereby describe an instance of diastereoselective trifluoromethanesulfonic acid catalyzed 1,3-dipolar cycloaddition of a trifluoromethylated azomethine imine with α,β-ethenyl ketones. Using two different reaction conditions, reaction of trifluoroacetaldehyde phenylhydrazone and chalcone derivatives gave polysubstituted pyrazolidines and pyrazolines derivatives with efficiency and high diastereoselectivity.

Key words

pyrazolines - hydrazone - copper triflate - trifluoromethanesulfonic acid - cycloaddition

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References

1a Padwa A. 1,3-Dipolar Cycloaddition Chemistry Vol. I: John Wiley & Sons; New York: 1984.

1b Padwa A. In Comprehensive Organic Synthesis Vol. 4: Trost BM. Fleming I. Pergamon Press; New York: 1991. p.1069-1109

1c Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry toward Heterocycles and Natural Products, In The Chemistry of Heterocyclic Compounds Vol. 59: Padwa A. Pearson WH. John Wiley & Sons; New York: 2002.

1d Nájera C. Sansano JM. Curr. Org. Chem. 2003, 7: 1105

1e Kanemasa S. Synlett 2002, 1371

1f Gothelf KV. In Cycloaddition Reactions in Organic Synthesis Kobayashi S. Jørgensen KA. Wiley-VCH; Weinheim: 2002. p.211-245

2a Curtius T. Chem. Ber. 1883, 16: 2230

2b Buchner E. Chem. Ber. 1888, 21: 2637

2c Beckmann E. Chem. Ber. 1890, 23: 3331

2d Werner A. Buss H. Chem. Ber. 1894, 27: 2193

3a Black DStC. Crozier RF. Davis VC. Synthesis 1975, 205

3b Bianchi G. DeMicheli C. Gandolfi R. In The Chemistry of Double-Bonded Functional Groups, Part 1 Patai S. Wiley; London: 1977. Chap. 6. p.369-532

3c Balasubramanian N. Org. Prep. Proced. Int. 1985, 17: 25

3d Confalone PN. Huie EM. Org. React. 1988, 36: 1

3e Frederickson M. Tetrahedron 1997, 53: 403

3f Gothelf KV. Jørgensen KA. Chem. Rev. 1998, 98: 863

3g Gothelf KV. Jørgensen KA. Chem. Commun. 2000, 1449

3h Jones RCF. Martin JN. Smith P. Gelbrich T. Light ME. Hursthouse MB. Chem. Commun. 2000, 1949

3i Lang SA. Lin Y.-I. In Comprehensive Heterocyclic Chemistry Vol. 6: Katritzky AR. Rees CW. Pergamon Press; Oxford: 1984. p.1-130

3j Caramella P. Grünanger P. In 1,3-Dipolar Cycloaddition Chemistry Vol. 1: Padwa A. Wiley-Interscience; New York: 1984. Chap. 3. p.291

3k Torssell KBG. Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis VCH; Weinheim: 1988.

3l Curran DP. In Advances in Cycloaddition Vol. 1: Curran DP. Jai Press; Connecticut: 1988. p.129-189

3m Kozikowski AP. Acc. Chem. Res. 1984, 17: 410

3n Jäger V. Grund H. Angew. Chem., Int. Ed. Engl. 1976, 15: 50

3o Jäger V. Grund H. Buss V. Schwab W. Müller I. Schohe R. Franz R. Ehrler R. Bull. Soc. Chim. Belg. 1983, 92: 1039

3p Jäger V. Müller I. Schohe R. Frey M. Ehrler R. Häfele B. Schröter D. Lect. Heterocycl. Chem. 1985, 8: 79

4a Pandey G. Banerjee P. Gadre SR. Chem. Rev. 2006, 106: 4484

4b Cabrera S. Arrayas RG. Carretero JC. J. Am. Chem. Soc. 2005, 127: 16394

4c Chen C. Li XD. Schreiber SL. J. Am. Chem. Soc. 2003, 125: 10174

4d Chen XH. Zhang WQ. Gong LZ. J. Am. Chem. Soc. 2008, 130: 5652

4e Longmire JM. Wang B. Zhang XM. J. Am. Chem. Soc. 2002, 124: 13400

4f Lopez-Perez A. Adrio J. Carretero JC. J. Am. Chem. Soc. 2008, 130: 10084

4g Saito S. Tsubogo T. Kobayashi S. J. Am. Chem. Soc. 2007, 129: 5364

4h Tsubogo T. Saito S. Seki K. Yamashita Y. Kobayashi S. J. Am. Chem. Soc. 2008, 130: 13321

4i Wang CJ. Liang G. Xue ZY. Gao F. J. Am. Chem. Soc. 2008, 130: 17250

4j Yan XX. Peng Q. Li Q. Zhang K. Yao J. Hou XL. Wu YD. J. Am. Chem. Soc. 2008, 130: 14362

4k Zeng W. Chen GY. Zhou YG. Li YX. J. Am. Chem. Soc. 2007, 129: 750

4l Sibi MP. Soeta T. Jasperse CP. Org. Lett. 2009, 11: 5366

4m Houk KN. González J. Li Y. Acc. Chem. Res. 1995, 28: 81

4n Firestone RA. J. Org. Chem. 1968, 33: 2285

4o Firestone RA. J. Chem. Soc. A 1970, 1570

4p Firestone RA. J. Org. Chem. 1972, 37: 2181

4q Firestone RA. Tetrahedron 1977, 33: 3009

4r Huisgen R. J. Org. Chem. 1968, 33: 2291

4s Huisgen R. J. Org. Chem. 1976, 41: 403

4t Escolano C. Duque MD. Vazquez S. Curr. Org. Chem. 2007, 11: 741

5a Tanaka K. Kato T. Ukaji Y. Inomata K. Heterocycles 2010, 80: 887

5b Maiti DK. Chatterjee N. Pandit P. Hota SK. Chem. Commun. 2010, 46: 2022

5c Hashimoto T. Maeda Y. Omote M. Nakatsu H. Maruoka K. J. Am. Chem. Soc. 2010, 132: 4076

5d Sibi MP. Rane D. Stanley LM. Soeta T. Org. Lett. 2008, 10: 2971

5e Jones RCF. Hollis SJ. Iley JN. ARKIVOC 2007, (v): 152

5f Gergely J. Morgan JB. Overman LE. J. Org. Chem. 2006, 71: 9144

5g Wang YZ. Vera CIR. Lin Q. Org. Lett. 2007, 9: 4155

5h Wamhoff H. Zahran M. Synthesis 1987, 876

5i Kanemasa S. Kobayashi S. Bull. Chem. Soc. Jpn. 1993, 66: 2685

5j Bourgeois P. Cantegril R. Chene A. Gelin J. Mortier J. Moyroud J. Synth. Commun. 1993, 23: 3195

5k Qi XB. Ready JM. Angew. Chem. Int. Ed. 2007, 46: 3242

5l Barluenga J. Fernandez-Mari F. Viado AL. Aguilar E. Olano B. Garcia-Granda S. Moya-Rubiera C. Chem. Eur. J. 1999, 5: 883

5m Mish MR. Guerra FM. Carreira EM. J. Am. Chem. Soc. 1997, 119: 8379

6a Grigg R. Kemp J. Thompson N. Tetrahedron Lett. 1978, 19: 2827

6b Fevre GL. Sinbandhit S. Hamelin J. Tetrahedron 1979, 35: 1821

6c Fouchet B. Joucla M. Hauelin J. Tetrahedron Lett. 1981, 22: 1333

6d Fevre GL. Hamelin J. Tetrahedron 1980, 36: 887

6e Grigg R. Dowling M. Jordan MW. Sridharan V. Thianpatanagul S. Tetrahedron 1987, 43: 5873

6f Shimizu T. Hayashi Y. Miki M. Teramura K. J. Org. Chem. 1987, 52: 2277

6g Kobayashi S. Shimizu H. Yamashita Y. Ishitani H. Kobayashi J. J. Am. Chem. Soc. 2002, 124: 13678

6h Kobayashi S. Hirabayashi R. Shimizu H. Ishitani H. Yamashita Y. Tetrahedron Lett. 2003, 44: 3351

6i Yamashita Y. Kobayashi S. J. Am. Chem. Soc. 2004, 126: 11279

6j Gergely J. Morgan JB. Overman LE.
J. Org. Chem. 2006, 71: 9144

6k Deng XH. Mani NS. Org. Lett. 2008, 10: 1307

6l Frank E. Mucsi Z. Zupko I. Rethy B. Falkay G. Schneider G. Wolfling J. J. Am. Chem. Soc. 2009, 131: 3894

6m LaLonde RL. Wang ZJ. Mba M. Lackner AD. Toste FD. Angew. Chem. Int. Ed. 2010, 49: 598

7a Deng XH. Mani NS. Org. Lett. 2006, 8: 3505

7b Deng XH. Mani NS. J. Org. Chem. 2008, 73: 2412

8a Roberts JD. Webb RL. McElhill EA. J. Am. Chem. Soc. 1950, 72: 408

8b Banks RE. Tatlow CJ. In Organofluorine Chemistry, Principles and Commercial Applications Banks RE. Smart BE. Tatlow CJ. Plenum Press; New York: 1994.

8c Koppel IA. Pihl V. Koppel J. Anvia F. Taft RW. J. Am. Chem. Soc. 1994, 116: 8654

8d Raabe G. Gais H.-J. Fleischhauser J. J. Am. Chem. Soc. 1996, 118: 4622

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