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Synthesis 2017; 49(14): 3165-3170
DOI: 10.1055/s-0036-1589015
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 3-Formylbenzenesulfonyl Chloride Derivatives

Xuefei Bao
Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, P. R. of China   Email: chenguoliang@syphu.edu.cn
,
Ziao Liu
Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, P. R. of China   Email: chenguoliang@syphu.edu.cn
,
Xinjie Liang
Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, P. R. of China   Email: chenguoliang@syphu.edu.cn
,
Dake Song
Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, P. R. of China   Email: chenguoliang@syphu.edu.cn
,
Tao Shi
Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, P. R. of China   Email: chenguoliang@syphu.edu.cn
,
Xuan Zhao
Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, P. R. of China   Email: chenguoliang@syphu.edu.cn
,
Changshun Bao
Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, P. R. of China   Email: chenguoliang@syphu.edu.cn
,
Guoliang Chen*
Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, P. R. of China   Email: chenguoliang@syphu.edu.cn
› Author AffiliationsSupported by: Discipline Construction Program of Shenyang Pharmaceutical University (52134606)
Supported by: Natural Science Foundation of Liaoning Province (201602707)
Further Information

Publication History

Received: 22 January 2017

Accepted after revision: 01 April 2017

Publication Date:
05 May 2017 (online)

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Abstract

A synthetic route to 3-formylbenzenesulfonyl chloride derivatives from the corresponding benzaldehydes has been developed. The key step in this procedure is the conversion of aldehyde bisulfite adducts to target compounds via a two-stage reaction in the presence of Na2SO4. A series of 3-formylbenzenesulfonyl chloride derivatives were prepared by this method and identified by chemical derivatization method.

Key words

3-formylbenzenesulfonyl chloride - aldehyde sodium bisulfite - chlorosulfonation - two-stage reaction - chemical derivatization method

Supporting Information

    Supporting information for this article is available online at https://doi.org /10.1055/s-0036-1589015.
  • Supporting Information

Primary Data

    Primary data for this article are available online at http://www.thieme-connect.com/ejournals/toc/synthesis and can be cited using the following DOI: 10.4125/pd0093th.

  • Primary Data
 

  • References

    • 1a Finn PW. Bandara M. Butcher C. Finn A. Hollinshead R. Khan N. Law N. Murthy S. Romero R. Watkins C. Andrianov V. Bokaldere RM. Dikovska K. Gailite V. Loza E. Piskunova I. Starchenkov I. Vorona M. Kalvinsh I. Helv. Chim. Acta 2005; 88: 1630
      Crossref
    • 1b Cervi G. Magnaghi P. Asa D. Avanzi N. Badari A. Borghi D. Caruso M. Cirla A. Cozzi L. Felder E. Galvani A. Gasparri F. Lomolino A. Magnuson S. Malgesini B. Motto I. Pasi M. Rizzi S. Salom B. Sorrentino G. Troiani S. Valsasina B. O’Brien T. Isacchi A. Donati D. D’Alessio R. J. Med. Chem. 2014; 57: 10443
      CrossrefPubMed
  • 2 Oliveira ME. Cenzi G. Nunes RR. Andrighetti CR. Valadão DM. S. Reis C. Simões CM. O. Nunes RJ. Júnior MC. Taranto AJ. Sanchez BA. M. Viana GH. R. Varotti FP. Molecules 2013; 18: 15276
    CrossrefPubMed
  • 3 Paal M. Ruehter G. Schotten T. Patent PCT Int. Appl. WO 0078726, 2000
    PubMed
  • 4 Yamaguchi Y. Menear K. Cohen N. Maha R. Cumin F. Schnell C. Wood JM. Maibaum J. Bioorg. Med. Chem. Lett. 2009; 19: 4863
    CrossrefPubMed
  • 5 Lowe C. Dyke HJ. Hanghan AF. Galvin FC. A. Morgan T. Picken CL. Patent PCT Int. Appl. WO 0174786, 2001
    PubMed
  • 6 Zimmerman SS. Khatri A. Garnier-Amblard EC. Mullasseril P. Kurtkaya NL. Gyoneva S. Hansen KB. Traynelis SF. Liotta DC. J. Med. Chem. 2014; 57: 2334
    CrossrefPubMed
  • 7 Wang Q. Luo J. Cao Y. Zhang L. Li C. Yuan Q. Faming Zhuanli Shenqing Gongkai Shuomingshu Patent CN105367455, 2016
    PubMed
  • 8 Achmatowicz O. Balicki R. Chmielowiec U. Zaworska A. Szelejewski W. Magielka S. Glowacka S. Wysoczynska M. Dzikowska J. Bober L. Landsberg J. Falkowski C. Roznerski Z. Marczak B. Kempa A. Patent PCT Int. Appl. WO 0122918, 2001
    PubMed
  • 9 Zhao T. Grützke M. Götz KH. Druzhenkob T. Huhn T. Dalton Trans. 2015; 44: 16475
    CrossrefPubMed
  • 10 Liu Y. Zhang Z. Faming Zhuanli Shenqing Gongkai Shuomingshu Patent CN1454892, 2003
    PubMed
  • 11 Bao X. Song D. Qiao X. Zhao X. Chen G. Org. Process Res. Dev. 2016; 20: 1482
    Crossref
  • 12 Wolfson A. Shokin O. Tavor D. J. Mol. Catal. A: Chem. 2005; 226: 69
    Crossref
  • 13 Lu J. Ma H. Han B. Lu B. Bao X. Faming Zhuanli Shenqing Gongkai Shuomingshu Patent CN 102633696 A, 2012
    PubMed
    • 14a Faul M. Larsen R. Levinson A. Tedrow J. Vounatsos F. J. Org. Chem. 2013; 78: 1655
      CrossrefPubMed
    • 14b Knight CJ. Millan DS. Moses IB. Robin AA. Selby MD. Org. Process Res. Dev. 2012; 16: 697
      Crossref
  • 15 Weston AW. Suter CM. Org. Synth. 1941; 21: 27
    Crossref
  • 17 Wei W. Cheng D. Liu J. Li Y. Ma Y. Li Y. Yu S. Zhang X. Li Z. Org. Biomol. Chem. 2016; 14: 8356
    CrossrefPubMed
  • 18 Marzolph G. Blank HU. Ger. Offen DE 3016186, 1981
    PubMed