Selective Synthesis of Unsymmetrical
Peroxides: Transition-Metal-Catalyzed Oxidation of Malononitrile
and Cyanoacetic Ester Derivatives by tert-Butyl Hydroperoxide
at the α-Position

Alexander O. Terent’ev; Dmitry A. Borisov; Vsevolod V. Semenov; Vladimir V. Chernyshev; Valery M. Dembitsky; Gennady I. Nikishin

doi:10.1055/s-0030-1260027

PAPER

Selective Synthesis of Unsymmetrical Peroxides: Transition-Metal-Catalyzed Oxidation of Malononitrile and Cyanoacetic Ester Derivatives by tert-Butyl Hydroperoxide at the α-Position

Alexander O. Terent’ev*^a, Dmitry A. Borisov^a, Vsevolod V. Semenov^a, Vladimir V. Chernyshev^b,c, Valery M. Dembitsky^d, Gennady I. Nikishin*^a
^a N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation
Fax: +7(499)1355328; e-Mail: terentev@ioc.ac.ru;
^b Department of Chemistry, , Moscow State University, 119992 Moscow, Russian Federation
^c A.N. Frumkin Institute of Physical Chemistry and Electrochemistry, 31 Leninsky prosp., 119991 Moscow, Russian Federation
^d Institute for Drug Research, P.O. Box 12065, Hebrew University, Jerusalem 91120, Israel

Abstract

Alle Artikel dieser Rubrik

Abstract

A novel method was developed for the selective oxidation of α-monosubstituted malononitrile and cyanoacetic ester derivatives at the α-position based on transition-metal-catalyzed reaction (Cu, Fe, Mn, Co) with tert-butyl hydroperoxide giving unsymmetrical peroxides in 63-94% yields. The method is facile, does not require large excesses of reagents, and is amenable to gram-scale synthesis.

Key words

peroxides - tert-butyl hydroperoxide - catalysis - oxidation - transition metals - malononitrile - cyanoacetic ester

Volltext

Referenzen

References

1a Jefford CW. Drug Discovery Today 2007, 12: 487

1b Opsenica DM. olaja BA. J. Serb. Chem. Soc. 2009, 74: 1155

1c Muregi FW. Ishih A. Drug Dev. Res. 2010, 71: 20

1d Muraleedharan KM. Avery MA. Drug Discovery Today 2009, 14: 793

1e O’Neil PM. Posner GH. J. Med. Chem. 2004, 47: 2945

1f Dong Y. Mini-Rev. Med. Chem. 2002, 2: 113

1g Vennerstrom JL. Fu H.-N. Ellis WY. Ager AL. Wood JK. Andersen SL. Gerena L. Milhous WK. J. Med. Chem. 1992, 35: 3023

1h Barton V. Ward SA. Chadwick J. Hill A. O’Neill PM. J. Med. Chem. 2010, 53: 4555

1i Ghorai P. Dussault PH. Hu C. Org. Lett. 2008, 10: 2401

1j Gelb MH. Curr. Opin. Chem. Biol. 2007, 11: 440

1k Tolstikov GA. Tolstikov AG. Tolstikova OV. Russ. Chem. Rev. 1996, 65: 769

2a Hamann H.-J. Hecht M. Bunge A. Gogol M. Liebscher J. Tetrahedron Lett. 2011, 52: 107

2b Kumar N. Khan SI. Rajalakshmi BG. Kumaradhas P. Rawat DS. Bioorg. Med. Chem. 2009, 17: 5632

2c Kim H.-S. Shibata Y. Wataya Y. Tsuchiya K. Masuyama A. Nojima M. J. Med. Chem. 1999, 42: 2604

2d Atheaya H. Khan SI. Mamgain R. Rawat DS. Bioorg. Med. Chem. Lett. 2008, 18: 1446

2e Jin H.-X. Liu H.-H. Zhang Q. Wu Y. Tetrahedron. Lett. 2005, 46: 5767

2f Bellot F. Coslédan F. Vendier L. Brocard J. Meunier B. Robert A. J. Med. Chem. 2010, 53: 4103

2g Jin H.-X. Zhang Q. Kim H.-S. Wataya Y. Liu H.-H. Wu Y. Tetrahedron 2006, 62: 7699

2h Iskra J. Bonnet-Delpon D. Bégué J.-P. Tetrahedron Lett. 2003, 44: 6309

2i Singh C. Hassam M. Naikade NK. Verma VP. Singh AS. Puri SK. J. Med. Chem. 2010, 53: 7587

2j Solaja BA. Terzic N. Pocsfalvi G. Genena L. Tinant B. Opsenica D. Milhous WK. J. Med. Chem. 2002, 45: 3331

2k Ellis GL. Amewu R. Hall C. Rimmer K. Ward SA. O’Neill PM. Bioorg. Med. Chem. Lett. 2008, 18: 1720

2l McCullough KJ. Wood JK. Bhattacharjee AK. Dong Y. Kyle DE. Milhous WK. Vennerstrom JL. J. Med. Chem. 2000, 43: 1246

3a Keiser J. Veneziano V. Rinaldi L. Mezzino L. Duthaler U. Cringoli Gi. Res. Vet. Sci. 2010, 88: 107

3b Shuhua X. Tanner M. N’Goran EK. Utzinger J. Chollet J. Bergquist R. Chen M. Zheng J. Acta Trop. 2002, 82: 175

3c Keiser J. Brun R. Fried B. Utzinger J. Antimicrob. Agents Chemother. 2006, 50: 803

3d Keiser J. Xiao SH. Tanner M. Utzinger J. J. Antimicrob. Chemother. 2006, 57: 1139

3e Keiser J. Utzinger J. Tanner M. Dong Y. Vennerstrom JL. J. Antimicrob. Chemother. 2006, 58: 1193

3f Keiser J. Xiao S.-H. Dong Y. Utzinger J. Vennerstrom JL. J. Parasitol. 2007, 93: 1208

4a Ellis GL. Amewu R. Sabbani S. Stocks PA. Shone A. Stanford D. Gibbons P. Davies J. Vivas L. Charnaud S. Bongard E. Hall C. Rimmer K. Lozanom S. Jesús M. Gargallo D. Ward SA. O’Neill PM.
J. Med. Chem. 2008, 51: 2170

4b Amewu R. Stachulski AV. Ward SA. Berry NG. Bray PG. Davies J. Labat G. Vivas L. O’Neill PM. Org. Biomol. Chem. 2006, 4: 4431

4c Dong Y. Tang Y. Chollet J. Matile H. Wittlin S. Charman SA. Charman WN. Tomas JS. Scheurer C. Snyder C. Scorneaux B. Bajpai S. Alexander SA. Wang X. Padmanilayam M. Cheruku SR. Brun R. Vennerstrom JL. Bioorg. Med. Chem. 2006, 14: 6368

4d Singh C. Malik H. Puri SK. Bioorg. Med. Chem. Lett. 2004, 14: 459

5a Dembitsky VM. Gloriozova TA. Poroikov VV. Mini-Rev. Med. Chem. 2007, 7: 571

5b Jung M. Kim H. Lee K. Park M. Mini-Rev. Med. Chem. 2003, 3: 159

5c Kim J. Park EJ. Curr. Med. Chem.: Anti-Cancer Agents 2002, 2: 485

5d Dembitsky VM. Eur. J. Med. Chem. 2008, 43: 223

5e Dembitsky VM. Gloriozova TA. Poroikov VV. Mini-Rev. Med. Chem. 2005, 5: 319

5f Terzić N. Opsenica D. Milić D. Tinant B. Smith KS. Milhous WK. Šolaja BA. J. Med. Chem. 2007, 50: 5118

5g i˛ak . Juranić Z. Opsenica D. Šolaja BA. Invest. New Drugs 2009, 27: 432

6a Barbosa LCA. Maltha CRA. Cusati RC. Teixeira RR. Rodrigues FF. Silva AA. Drew MGB. Ismail FMD. J. Agric. Food Chem. 2009, 57: 10107

6b Macías FA. Chinchilla N. Varela RM. Molinillo JMG. Steroids 2006, 71: 603

6c Barbosa LCA. Pereira UA. Teixeira RR. Maltha CRA. Fernandes SA. Forlani G. J. Agric. Food Chem. 2008, 56: 9434

6d Chen PK. Leather GR. J. Chem. Ecol. 1990, 16: 1867

7a Matyáš R. Šelešovský J. J. Hazard. Mater. 2009, 165: 95

7b Rabenecker P. Pinkwart K. Propellants, Explos., Pyrotech. 2009, 34: 274

7c Burks RM. Hage DS. Anal. Bioanal. Chem. 2009, 395: 301

7d Dubnikova F. Kosloff R. Almog J. Zeiri Y. Boese R. Itzhaky H. Alt A. Keinan E. J. Am. Chem. Soc. 2005, 127: 1146

7e Meyer R. Explosives Verlag Chemie; Weinheim: 1977.

7f Denekamp C. Gottlieb L. Tamiri T. Tsoglin A. Shilav R. Kapon M. Org. Lett. 2005, 7: 2461

7g Muller D. Levy A. Shelef R. Abramovich-Bar S. Sonenfeld D. Tamiri T. J. Forensic Sci. 2004, 49: 935

8a Terent’ev AO. Borisov DA. Chernyshev VV. Nikishin GI. J. Org. Chem. 2009, 74: 3335

8b Terent’ev AO. Borisov DA. Yaremenko IA. Chernyshev VV. Nikishin GI. J. Org. Chem. 2010, 75: 5065

9a Kharasch MS. Pauson P. Nudenberg W. J. Org. Chem. 1953, 18: 322

9b Kharasch MS. Fono A. J. Org. Chem. 1958, 23: 324

9c Kharasch MS. Fono A. J. Org. Chem. 1959, 24: 72

10a Shul’pin GB. Gradinaru J. Kozlov YN. Org. Biomol. Chem. 2003, 1: 3611

10b Araneo S. Fontana F. Minisci F. Recupero F. Serri A. J. Chem. Soc., Chem. Commun. 1995, 1399

10c Bravo A. Bjørsvik H.-R. Fontana F. Liguori L. Minisci F. J. Org. Chem. 1997, 62: 3849

10d Meder MB. Gade LH. Eur. J. Inorg. Chem. 2004, 2716

10e Vida JA. Samour CM. O’Dea MH. Wang TST. Reinhard JF. J. Med. Chem. 1974, 17: 1194

10f Li Z. Li C.-J. J. Am. Chem. Soc. 2005, 127: 6968

10g Punniyamurthy T. Rout L. Coord. Chem. Rev. 2008, 252: 134

11a Treibs W. Pellmann G. Chem. Ber. 1954, 87: 1201

11b Saussine L. Brazi E. Robine A. Mimoun H. Fischer J. Weiss R. J. Am. Chem. Soc. 1985, 107: 3534

12a Leising RA. Norman RE. Que L. Inorg. Chem. 1990, 29: 2553

12b Leising RA. Zang Y. Que L.
J. Am. Chem. Soc. 1991, 113: 8555

12c Kojima T. Leising RA. Yan S. Que L. J. Am. Chem. Soc. 1993, 115: 11328

12d Leising RA. Kim J. Perez MA. Que L. J. Am. Chem. Soc. 1993, 115: 9524

12e Arends IWCE. Ingold KU. Wayner DDM. J. Am. Chem. Soc. 1995, 117: 4710

13 Minisci F. Fontana F. Araneo S. Recupero F. J. Chem. Soc., Chem. Commun. 1994, 1823

14 Minisci F. Fontana F. Araneo S. Recupero F. Banfi S. Quici S. J. Am. Chem. Soc. 1995, 117: 226

15a Murahashi S.-I. Zhang D. Chem. Soc. Rev. 2008, 37: 1490

15b Murahashi S.-I. Naota T. Kuwabara T. Saito T. Kumobayashi H. Akutagawa S. J. Am. Chem. Soc. 1990, 112: 7820

15c Murahashi S.-I. Naota T. Yonemura K. J. Am. Chem. Soc. 1988, 110: 8256

16a Heathcock CH. Mahaim C. Schlecht MF. Utawanit T. J. Org. Chem. 1984, 49: 3264

16b Ancerewicz J. Vogel P. Helv. Chim. Acta 1996, 79: 1393

16c Rubottom GM. Vazquez MA. Pelegrina DR. Tetrahedron Lett. 1974, 15: 4319

16d Andriamialisoa RZ. Langlois N. Langlois Y. J. Org. Chem. 1985, 50: 961

17a Adam W. Smerz AK. Tetrahedron 1996, 52: 5799

17b Barrett AGM. Head J. Smith ML. Stock NS. White AJP. Williams DJ. J. Org. Chem. 1999, 64: 6005

17c Smith AMR. Billen D. Hii KKM. Chem. Commun. 2009, 3925

18a Li D. Schröder K. Bitterlich B. Tse MK. Beller M. Tetrahedron Lett. 2008, 49: 5976

18b Abu-Omar MM. Espenson JH. Organometallics 1996, 15: 3543

19a Yoshioka M. Nishioka T. Hasegawa T. J. Org. Chem. 1993, 58: 278

19b Christoffers J. Werner T. Frey W. Baro A. Eur. J. Org. Chem. 2003, 4879

19c Rahman MT. Nishino H. Org. Lett. 2003, 5: 2887

19d Irie H. Katakawa J. Tomita M. Mizuno Y. Chem. Lett. 1981, 637

19e Wasserman HH. Pickett JE. J. Am. Chem. Soc. 1982, 104: 4695

19f Hiroya K. Ogasawara K. Chem. Commun. 1999, 2197

19g Watanabe T. Ishikawa T. Tetrahedron Lett. 1999, 40: 7795

19h Christoffers J. J. Org. Chem. 1999, 64: 7668

19i Baucherel X. Levoirier E. Uziel J. Juge S. Tetrahedron Lett. 2000, 41: 1385

19j Richardson AM. Chen C.-H. Snider BB. J. Org. Chem. 2007, 72: 8099

19k Monguchi Y. Takahashi T. Iida Y. Fujiwara Y. Inagaki Y. Maegawa T. Sajiki H. Synlett 2008, 2291

20a Shu X.-Z. Xia X.-F. Yang Y.-F. Ji K.-G. Liu X.-Y. Liang Y.-M. J. Org. Chem. 2009, 74: 7464

20b Li Z. Bohle DS. Li C.-J. Proc. Natl. Acad. Sci. U.S.A. 2006, 103: 8928

21a Li C.-J. Acc. Chem. Res. 2009, 42: 335

21b Li Z. Li C.-J. J. Am. Chem. Soc. 2006, 128: 56

21c Yoo W.-J. Li C.-J. J. Org. Chem. 2006, 71: 6266

21d Li Z. Cao L. Li C.-J. Angew. Chem. Int. Ed. 2007, 46: 6505

21e Borduas N. Powell DA. J. Org. Chem. 2008, 73: 7822

21f Correia CA. Li C.-J. Tetrahedron Lett. 2010, 51: 1172

22 Mohamadin AM. J. Inorg. Biochem. 2001, 84: 97

23a Kujime M. Hikichi S. Akita M. Inorg. Chim. Acta 2003, 350: 163

23b Min’ko YA. Belina NV. Sushev VV. Fukin GK. Bubnov MP. Kornev AN. J. Organomet. Chem. 2007, 692: 4157

23c Bruce MI. Buntine MA. Costuas K. Ellis BG. Halet J.-F. Low PJ. Skelton BW. White AH. J. Organomet. Chem. 2004, 689: 3308

23d Kukushkin VYu. Armando JL. Inorg. Chim. Acta 2005, 358: 1

23e Banerjee A. Banu KS. Podder N. Mukherjee M. Ghosh M. Suresh E. Das D. J. Mol. Struct. 2008, 888: 62

23f Yang L.-Z. Li Y. Zhuang X.-M. Jiang L. Chen J.-M. Luck RL. Lu T.-B. Chem. Eur. J. 2009, 15: 12399

24a Minisci F. Fontana F. Araneo S. Recupero F. Zhao L. Synlett 1996, 119

24b Avila DV. Ingold KU. Lusztyk J. Green WH. Procopio DR. J. Am. Chem. Soc. 1995, 117: 2929

24c Paul H. Small RD. Scaiano JC.
J. Am. Chem. Soc. 1978, 100: 4520

24d Barton DHR. Le Gloahec VN. Patin H. Launay F. New J. Chem. 1998, 559

25a Kratochvil B. Zatko DA. Markuszewski R. Anal. Chem. 1966, 38: 770

25b Kratochvil B. Quirk PF. Anal. Chem. 1970, 42: 492

25c Mruthyunjaya HC. Murthy ARV. Indian J. Chem. 1969, 7: 403

26 Mruthyunjaya HC. Murthy ARV. Indian J. Chem. 1973, 11: 481

27a Senne JK. Kratochvil B. Anal. Chem. 1971, 43: 79

27b Persson I. Penner-Hahn JE. Hodgson KO. Inorg. Chem. 1993, 32: 2497

28 Dunham JC. Richardson AD. Sammelson RE. Synthesis 2006, 680

29 Ramachary DB. Reddy GB. Org. Biomol. Chem. 2006, 4: 4463

30 Abd El Samii ZKM. Al Ashmawy MI. Mellor JM. J. Chem. Soc., Perkin Trans. 1 1988, 2523

31 Seela F. Lüpke U. Chem. Ber. 1977, 110: 1462

32 Koelsch CF. J. Am. Chem. Soc. 1943, 65: 2458

Zusatzmaterial

Supporting Information