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Synthesis 2012(2): 283-289  
DOI: 10.1055/s-0031-1289647
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

An Efficient and Practical Synthesis of Aryl and Hetaryl α-Keto Esters

Akula Raghunadha, Suresh Babu Meruvaa, Nuka Anil Kumara, Gudla Santosh Kumara, L. Vaikunta Raob, U. K. Syam Kumar*a
a Technology Development Centre, Custom Pharmaceutical Services, Dr. Reddy’s Laboratories Ltd., Miyapur, Hyderabad, 500 049, India
Fax: +91(40)23045439; e-Mail: syam_kmr@yahoo.com;
b Gitam University, Gandhi Nagar, Rushikonda, Visakhapatanam 530 045, India
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Publikationsverlauf

Received 14 July 2011
Publikationsdatum:
16. Dezember 2011 (online)

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Abstract

A general and highly efficient method was developed for the synthesis of α-keto esters by oxidative esterification of 2,2-dibromo-1-(het)arylethanones by sequential treatment with dimethyl sulfoxide and an alkanol. The versatility of the reaction was established by synthesizing a range of α-keto esters by treatment of 2,2-dibromoethanones, derived from aryl or hetaryl ketones, with di­methyl sulfoxide and a cyclic or acyclic primary or secondary alcohol. The mechanism of the reaction was established by means of a detailed study.

Key words

ketones - esters - oxidations - esterifications - alcohols

    References

  • 1 Li L.-S. Wu Y.-L. Tetrahedron Lett.  2002,  43:  2427 
    Suche in Google Scholar
  • 2a Patel DV. Reilly GK. Ryono DE. Free CA. Smith SA. Petrillo EW. J. Med. Chem.  1993,  36:  2431 
    Suche in Google Scholar
  • 2b O’Cain TD. Rich DH. J. Med. Chem.  1992,  35:  451 
    Suche in Google Scholar
  • 2c Iwanowicz EJ. Lin J. Roberts DGM. Michel IM. Seiler SM. Bioorg. Med. Chem. Lett.  1992,  2:  1607 
    Suche in Google Scholar
  • 2d Angelastro MR. Mehdi S. Burkhart JP. Peet NP. Bey P. J. Med. Chem.  1990,  33:  11 
    Suche in Google Scholar
  • 2e Yuan W. Wong CH. Haeggstroem JZ. Wetterholm A. Samuelsson B. J. Am. Chem. Soc.  1992,  114:  6552 
    Suche in Google Scholar
  • 2f Yuan W. Munoz B. Wong CH. Haeggstroem JZ. Wetterholm A. Samuelsson B. J. Med. Chem.  1993,  36:  211 
    Suche in Google Scholar
  • 2g Photis JM. Tetrahedron Lett.  1980,  21:  3539 
    Suche in Google Scholar
  • 2h Valentine D. Scott JW. Synthesis  1978,  329 
  • 3 Schulte K, and Meinzinger E. inventors; DE  949,521.  ; Chem. Abstr. 1958, 52, 19024
  • 4a Babudri F. Fiandanese V. Marchese G. Punzi A. Tetrahedron Lett.  1996,  42:  13513 
    Suche in Google Scholar
  • 4b Babudri F. Fiandanese V. Marchese G. Punzi A. Tetrahedron Lett.  1995,  36:  7305 
    Suche in Google Scholar
  • 5 Izawa Y. Tomioka H. Natsume M. Beppu S. Tsuji H. J. Org. Chem.  1980,  45:  4835 
    Suche in Google Scholar
  • 6a Ozawa V. Kawasaki N. Yamamoto T. Yamamoto A. Chem. Lett.  1985,  567 
  • 6b Hiroshi D, Sadao D, and Kazuo Z. inventors; JP  60-19750.  ; Chem. Abstr. 1985, 103, 5904c
  • 6c Sakakura T. Yamashita H. Kobayashi T. Hayashi T. Tanaka M. J. Org. Chem.  1987,  52:  5733 
    Suche in Google Scholar
  • 7 Micetich RG. Org. Prep. Proced. Int.  1970,  2:  249 
    Suche in Google Scholar
  • 8 Photis JM. Tetrahedron Lett.  1980,  21:  3539 
    Suche in Google Scholar
  • 9 Corey EJ. Erickson BW. J. Org. Chem.  1971,  36:  3553 
    Suche in Google Scholar
  • 10a Che C.-M. Yu W.-Y. Chan P.-M. Cheng W.-C. Peng S.-M. Lau K.-C. Li W.-K. J. Am. Chem. Soc.  2000,  122:  11380 
    Suche in Google Scholar
  • 10c Dayan S. Ben-David I. Rozen S. J. Org. Chem.  2000,  65:  8816 
    Suche in Google Scholar
  • 10d Walsh CJ. Mandal BK. J. Org. Chem.  1999,  64:  6102 
    Suche in Google Scholar
  • 10e Präler OC. Sauer J. Tetrahedron Lett.  1998,  39:  8821 
    Suche in Google Scholar
  • 10f Zibuck R. Seebach D. Helv. Chim. Acta  1988,  71:  237 
    Suche in Google Scholar
  • 10g Torii S. Inokuchi T. Hirata Y. Synthesis  1987,  377 
  • 10h Lee DG. Lee EJ. Brown KC. ACS Symp. Ser.  1987,  326:  82 
    Suche in Google Scholar
  • 10i Wolfe S. Ingold CF. J. Am. Chem. Soc.  1983,  105:  7755 
    Suche in Google Scholar
  • 11 Yamada K. Kato M. Iyoda M. Hirata Y. J. Chem. Soc., Chem. Commun.  1973,  499 
  • 12 Burkhart JP. Peet NP. Bey P. Tetrahedron Lett.  1988,  29:  3433 
    Suche in Google Scholar
  • 13 Zhuang J. Wang C. Xie F. Zhang W. Tetrahedron  2009,  65:  9797 
    Suche in Google Scholar
  • 14 Das S. Bhowmick T. Punniyamurthy T. Dey D. Nath J. Chaudhuri MK. Tetrahedron Lett.  2003,  44:  4915 
    Suche in Google Scholar
  • 15a Shanmugapriya D. Shankar R. Satyanarayana G. Dahanukar VH. Syam Kumar UK. Vembu N. Synlett  2008,  2945 
  • 15b Klingenberg J. Org. Synth. Coll. Vol. IV   John Wiley & Sons; London: 1963.  p.110 
  • 15c Bigelow LA. Hanslick RS. Org. Synth. Coll. Vol. II   John Wiley & Sons; London: 1943.  p.244 
  • 16 Baer E. Kates M. J. Am. Chem. Soc.  1945,  47:  1482 
    Suche in Google Scholar
  • 17a Johnson CR. Jones MP. J. Org. Chem.  1967,  32:  2014 
    Suche in Google Scholar
  • 17b Johnson CR. Rigau JJ. J. Am. Chem. Soc.  1969,  91:  5398 
    Suche in Google Scholar
  • 17c Khuddus MA. Swern D. J. Am. Chem. Soc.  1973,  95:  8393 
    Suche in Google Scholar
  • 17d Zhang J. Saito S. Koizumi T. J. Org. Chem.  1998,  63:  5265 
    Suche in Google Scholar
  • 17e Smith G. Winstein S. Tetrahedron  1958,  3:  317 
    Suche in Google Scholar
  • 18 Li W. Li J. Vincentis DD. Mansour TS. Tetrahedron Lett.  2004,  45:  1071 
    Suche in Google Scholar
  • 19 Schaefer JP. Corey EJ. J. Org. Chem.  1959,  24:  1825 
    Suche in Google Scholar
  • 20 Sakakura T. Yamashita H. Kobayashi T. Hayashi T. Tanaka M. J. Org. Chem.  1987,  52:  5733 
    Suche in Google Scholar
  • 21 Heaney F. Fenlon J. O’Mahony C. McArdle P. Cunningham D. Org. Biomol. Chem.  2003,  1:  4302 
    Suche in Google Scholar
  • 22 Hu S. Neckers DC. J. Org. Chem.  1996,  61:  6407 
    Suche in Google Scholar
  • 23 Muller AJ. Nishiyama K. Griffin GW. Ishikawa K. Gibson DM. J. Org. Chem.  1982,  47:  2342 
    Suche in Google Scholar
  • 24 Hjelmencrantz A. Berg U. J. Org. Chem.  2002,  67:  3585 
    Suche in Google Scholar
  • 25 Domagala JM. Tetrahedron Lett.  1980,  21:  4997 
    Suche in Google Scholar
  • 26 Gross H. Freiberg J. Chem. Ber.  1967,  100:  3777 
    Suche in Google Scholar
  • 27 Banerjee SK. Shankar R. Sachdeva OMP. Z. Phys. Chem. (Leipzig)  1986,  267:  931 
    Suche in Google Scholar
  • 28 Mallinger A. Le Gall T. Misokowski C. J. Org. Chem.  2009,  74:  1124 
    Suche in Google Scholar
  • 29a Fabbri C. Bietti M. Lanzalunga O. J. Org. Chem.  2005,  70:  2720 
    Suche in Google Scholar
  • 29b Raap M. Org. Prep. Proced. Int.  1971,  3:  167 
    Suche in Google Scholar
  • 29c Chrétien A. Chataigner I. L’Hélias N. Piettre SR. J. Org. Chem.  2003,  68:  7990 
    Suche in Google Scholar