Base-Catalyzed Addition of Ketones to Alkynes as a Key Step in the One-Pot Synthesis of 1-Formyl-2-pyrazolines

Elena Yu. Schmidt; Elena V. Ivanova; Inna V. Tatarinova; Nadezhda V. Semenova; Igor A. Ushakov; Boris A. Trofimov

doi:10.1055/s-0034-1378687

Synthesis, Table of Contents

Synthesis 2015; 47(09): 1329-1336
DOI: 10.1055/s-0034-1378687

paper

Base-Catalyzed Addition of Ketones to Alkynes as a Key Step in the One-Pot Synthesis of 1-Formyl-2-pyrazolines

Elena Yu. Schmidt

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 664033 Irkutsk, Russian Federation Email: boris_trofimov@irioch.irk.ru

,

Elena V. Ivanova

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 664033 Irkutsk, Russian Federation Email: boris_trofimov@irioch.irk.ru

,

Inna V. Tatarinova

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 664033 Irkutsk, Russian Federation Email: boris_trofimov@irioch.irk.ru

,

Nadezhda V. Semenova

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 664033 Irkutsk, Russian Federation Email: boris_trofimov@irioch.irk.ru

,

Igor A. Ushakov

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 664033 Irkutsk, Russian Federation Email: boris_trofimov@irioch.irk.ru

,

Boris A. Trofimov*

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 664033 Irkutsk, Russian Federation Email: boris_trofimov@irioch.irk.ru

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Abstract

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Abstract

The reaction of ketones with alkynes in the presence of potassium tert-butoxide and dimethylsulfoxide followed by the treatment of the reaction mixture with hydrazine hydrate and formic acid leads to 2-pyrazoline-1-carbaldehydes in up to 81% yield.

Key words

ketones - alkynes - 1-formyl-2-pyrazolines - superbases - vinylation

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References

References

1a Trofimov BA, Schmidt EYu, Ushakov IA, Zorina NV, Skital’tseva EV, Protsuk NI, Mikhaleva AI. Chem. Eur. J. 2010; 16: 8516
1b Trofimov BA, Schmidt EYu, Zorina NV, Ivanova EV, Ushakov IA, Mikhaleva AI. Adv. Synth. Catal. 2012; 354: 1813
1c Trofimov BA, Schmidt EYu, Zorina NV, Ivanova EV, Ushakov IA. J. Org. Chem. 2012; 77: 6880
1d Schmidt EYu, Zorina NV, Tarasova OA, Ushakov IA, Trofimov BA. Mendeleev Commun. 2013; 23: 204

2 Radin NS. Drug Dev. Res. 2008; 69: 15

For selected examples, see:

3a Hyde AM, Buchwald SL. Angew. Chem. Int. Ed. 2008; 47: 177
3b Sämann C, Knochel P. Synthesis 2013; 45: 1870
3c Mokar BD, Liu R.-S. Chem. Commun. 2014; 50: 8966
3d Jadhav AM, Gawade SA, Vasu D, Dateer RB, Liu R.-S. Chem. Eur. J. 2014; 20: 1813

4a Ohtsuka Y, Sasahara T, Oishi T. Chem. Pharm. Bull. 1982; 30: 1106 ; and references cited therein
4b Gohain M, Gogoi BJ, Prajapati D, Sandhu JS. New J. Chem. 2003; 27: 1038
4c Comprehensive Organic Functional Group Transformations II . Katritzky AR, Taylor RJ. K. Elsevier; Amsterdam: 2005
4d Iwasaki M, Morita E, Uemura M, Yorimitsu H, Oshima K. Synlett 2007; 167

5 Schmidt EYu, Tatarinova IV, Ivanova EV, Zorina NV, Ushakov IA, Trofimov BA. Org. Lett. 2013; 15: 104
6 See review: Shaaban MR, Mayhoub AS, Farag AM. Expert Opin. Ther. Patents 2012; 22: 253

For selected examples, see:

7a Ali MA, Shaharyar M, Siddiqui AA. Eur. J. Med. Chem. 2007; 42: 268
7b Shaharyar M, Siddiqui AA, Ali MA. Bioorg. Med. Chem. Lett. 2006; 16: 4571
7c Ali MA, Yar MS, Kumar M, Pandian GS. Nat. Prod. Res. 2007; 21: 575

For selected examples, see:

8a Bhat BA, Dhar K, Puri SC, Saxena AK, Shanmugavel M, Qazi GN. Bioorg. Med. Chem. Lett. 2005; 15: 3177
8b Shaharyar M, Abdullah MM, Bakht MA, Majeed J. Eur. J. Med. Chem. 2010; 45: 114
8c Kobayashi H, Dorai T, Holland JF, Ohnuma T. Cancer Res. 1994; 54: 1271
8d Rostom SA. F. Bioorg. Med. Chem. 2006; 14: 6475
8e Mazumdar T, DeVecchio J, Agyeman A, Shi T, Houghton JA. Cancer Res. 2011; 71: 5904

9a Singh P, Negi JS, Joshi née Pant G, Rawat MS. M. Molbank 2010; M650
9b Sid A, Lamara K, Mokhtari M, Ziani N, Mosset P. Eur. J. Chem. 2011; 2: 311

10a Insuasty B, Chamizo L, Minoz J, Tigreros A, Quiroga J, Abonia R, Nogueras M, Cobo J. Arch. Pharm. Chem. Life Sci. 2012; 345: 275
10b Rostom SA. F. M, Badr H, Abd El Razik HA, Ashour HM. A, Abdel-Wahab AE. Arch. Pharm. Chem. Life Sci. 2011; 344: 572

11a Rajput AP, Rajput SS. Int. J. Pharm. Pharm. Sci. 2011; 3: 346
11b Hassan SY. J. Braz. Chem. Soc. 2011; 22: 1286
11c Dajia B, Srivastava YK. Eur. J. Chem. 2007; 4: 187

12a Kendre MM, Baseer MA. Am. J. Adv. Drug Deliv. 2013; 1: 387
12b Azarifar D, Shaebanzadeh M. Molecules 2001; 7: 885

13 Khalil OM, Refaat HM. Orient. J. Chem. 2011; 27: 1581
14 Dimethyl Sulfoxide (DMSO), Technical Bulletin . Crown Zellerbach Chemical Products Division; Vancouver (Orchards) (WA, USA): 1985
15 Nagayama K, Kumar A, Wutrich K, Ernst RR. J. Magn. Reson. 1980; 40: 321
16 Wagner G, Wutrich K. J. Mol. Biol. 1982; 155: 347
17 Bodenhausen G, Ruben D. J. Chem. Phys. Lett. 1980; 69: 185
18 Bax A, Summers MF. J. Am. Chem. Soc. 1986; 108: 2093

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