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Synthesis 2004(18): 2999-3004  
DOI: 10.1055/s-2004-834888
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Convenient Synthesis of Novel 3-(Heterocyclylsulfonyl)propanoic Acids and their Amide Derivatives

Mikhail V. Dorogov, Sergey I. Filimonov, Dmitry B. Kobylinsky, Sergey A. Ivanovsky, Pavel V. Korikov, Mikhail Y. Soloviev, Maria Y. Khahina, Elena E. Shalygina, Dmitry V. Kravchenko, Alexandre V. Ivachtchenko*
Chemical Diversity Labs, Inc., 11558 Sorrento Valley Rd., Suite 5, San Diego, CA 92121, USA
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Publication History

Received 28 May 2004
Publication Date:
22 October 2004 (online)

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Abstract

A large number of novel 3-(heterocyclylsulfonyl)propanoic acids and their amide derivatives were prepared in good yields and excellent purity starting from the corresponding heterocyclic compounds. At first, chlorosulfonates were generated by reaction of initial heterocycles with various sulfonating and chlorinating agents followed by their conversion into sodium sulfinates. Treatment of sulfinates with acrylic acid smoothly afforded a series of sulfonylpropionates, which were used as convenient reagents for the preparation of a large number of the corresponding carboxamide derivatives.

Key words

3-(heterocyclylsulfonyl)propanoic acid - chlorosulfonates - heterocycles - parallel synthesis - libraries

    References

  • 1 Munroe JE. Shepherd TA. Jungheim LN. Hornback WJ. Hatch SD. Muesing MA. Wiskerchen M.-A. Su KS. Campanale KM. Baxter AJ. Colacino JM. Bioorg. Med. Chem. Lett.  1995,  5:  2897 
    CrossrefGoogle Scholar
  • 2a Tucker H. Chesterson GJ. J. Med. Chem.  1988,  31:  885 
    CrossrefGoogle Scholar
  • 2b Baxter AD. Bhogal R. Bird J. Keily JF. Manallack DT. Montana JG. Owen DA. Pitt WR. Watson RJ. Wills RE. Bioorg. Med. Chem. Lett.  2001,  11:  1465 
    CrossrefGoogle Scholar
  • 3 Becker DP. Barta TE. Bedell L. DeCrescenzo G. Freskos J. Getman DP. Hockerman SL. Li M. Mehta P. Mischke B. Munie GE. Swearingen C. Villamil CI. Bioorg. Med. Chem. Lett.  2001,  11:  2719 
    CrossrefGoogle Scholar
  • 4 Yamazaki Y. Akahane M. Kobayashi M. Kitazawa M. Kurashina Y. Iizuka K. Jpn. J. Pharmacol.  1993,  63:  219 ; Chem. Abstr., 1994, 120, 23328
    CrossrefGoogle Scholar
  • 5 Tyuneva IV. Filimonov SI. Soloviev MY. Balakin KV. Skorenko AV. Dorogov MV. Proc. Inst. Higher Edu.: Chem. Techn. (Russia)  2003,  46:  77 ; Chem. Abstr. 2004, 141, 54130
    Google Scholar
  • 6 Baru M, and Ivachtchenko A. inventors; Russian Patent  2180609.  ; Chem. Abstr. 2003, 138, 14907