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Synlett 2013; 24(7): 827-830
DOI: 10.1055/s-0032-1318456
DOI: 10.1055/s-0032-1318456
letter
Stereoselective Thermal Isomerization of Bis(spiropyrazolone)cyclopropanes into (4Z)-4-[(Pyrazol-4-yl)methylene]pyrazolones
Further Information
Publication History
Received: 30 January 2013
Accepted after revision: 22 February 2013
Publication Date:
14 March 2013 (online)
Abstract
Thermal isomerization of bis(spiropyrazolone)cyclopropanes in DMSO at 100 °C results in highly efficient formation of the corresponding 4-[(pyrazol-4-yl)methylene]pyrazolones in 90–98% yields after only five minutes. NMR and single-crystal X-ray diffraction analysis indicate stereoselective formation of the Z-isomers.
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References
- 1a Patai S, Rappoport Z. The Chemistry of the Cyclopropyl Group . Wiley; New York: 1987
- 1b Yu M, Pagenkopf BL. Tetrahedron 2005; 61: 321
- 1c Paquette LA. Chem. Rev. 1986; 86: 733
- 1d Dolbier WR, Battiste MA. Chem. Rev. 2003; 103: 1071
- 1e Fedorynski M. Chem. Rev. 2003; 103: 1099
-
2a Reissig H.-U, Zimmer R. Chem. Rev. 2003; 103: 1151
- 2b Rubin M, Rubina M, Gevorgyan V. Chem. Rev. 2007; 107: 3117
- 2c Chagarovskiy AO, Ivanova OA, Rakhmankulov ER, Budynina EM, Trushkov IV, Melnikova MY. Adv. Synth. Catal. 2010; 352: 3179
- 2d Hudlicky T, Reed JW. Angew. Chem. Int. Ed. 2010; 49: 4864
- 3a Wong HN. C, Hon M.-Y, Tse C.-W, Yip Y.-C, Tanko J, Hudlicky T. Chem. Rev. 1989; 89: 165
- 3b Baldwin JE. Chem. Rev. 2003; 103: 1197
- 4a Laroche C, Behr J.-B, Szymoniak J, Bertus P, Schutz C, Vogel P, Plantier-Royon R. Bioorg. Med. Chem. 2006; 14: 4047
- 4b Sandanayaka VP, Prashad AS, Yang Y, Williamson RT, Lin YI, Mansour TS. J. Med. Chem. 2003; 46: 2569
- 4c Jiang T, Kuhen KL, Wolff K, Yin H, Bieza K, Caldwell J, Bursulaya B, Wub TY.-H, He Y. Bioorg. Med. Chem. Lett. 2006; 16: 2105
- 4d Jiang T, Kuhen KL, Wolff K, Yin H, Bieza K, Caldwell J, Bursulaya B, Tuntland T, Zhang K, Karanewsky D, He Y. Bioorg. Med. Chem. Lett. 2006; 16: 2109
- 5a Wiley RH, Wiley P. Pyrazolones, Pyrazolidones, and Derivatives, In The Chemistry of Heterocyclic Compounds . Vol. 20. Weissberger A. Chap. VIII Interscience; New York: 1964
- 5b 100 Years of Pyrazolone Drugs: Agents and Actions Supplements – An Update. Vol. 19. Brune K. Birkhäuser; Basil: 1986: 355
- 6 Brogden RN. Drugs 1986; 32: Suppl. 4: 60
- 7a Ramajayam R, Tan K.-P, Liu H.-G, Liang P.-H. Bioorg. Med. Chem. 2010; 18: 7849
- 7b Sujatha K, Shanthi G, Selvam NP, Manoharan S, Perumal PT, Rajendran M. Bioorg. Med. Chem. Lett. 2009; 19: 4501
- 8a Zuliani V, Carmi C, Rivara M, Fantini M, Lodola A, Vacondio F, Bordi F, Plazzi PV, Cavazzoni A, Galetti M, Alfieri RR, Petronini PG, Mor M. Eur. J. Med. Chem. 2009; 3471
- 8b Ramajayam R, Tan K.-P, Liu H.-G, Liang P.-H. Bioorg. Med. Chem. Lett. 2006; 16: 2158
- 9 Itokawa M, Miyata T, Arai M. EP 2189537 A1, 2010
- 10 Elinson MN, Vereshchagin AN, Tretyakova EO, Bushmarinov IS, Nikishin GI. Synthesis 2011; 3015
- 11 Westoo G. Acta Chem. Scand. 1957; 11: 1359
- 12 Hennig L, Haessner R, Rissanen K. J. Prakt. Chem. 1989; 331: 681
- 13 Laikov DN. Chem. Phys. Lett. 2005; 416: 116
- 14 Laikov DN. Chem. Phys. Lett. 1997; 281: 151
- 15 Dolomanov OV, Bourhis LJ, Gildea RJ, Howard JA. K, Puschmann H. J. Appl. Cryst. 2009; 42: 339
- 16 Sheldrick G. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008; 64: 112
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