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 Affiliations
Supported 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)


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.

Supporting Information

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
    • 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
  • 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
  • 3 Paal M. Ruehter G. Schotten T. Patent PCT Int. Appl. WO 0078726, 2000
  • 4 Yamaguchi Y. Menear K. Cohen N. Maha R. Cumin F. Schnell C. Wood JM. Maibaum J. Bioorg. Med. Chem. Lett. 2009; 19: 4863
  • 5 Lowe C. Dyke HJ. Hanghan AF. Galvin FC. A. Morgan T. Picken CL. Patent PCT Int. Appl. WO 0174786, 2001
  • 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
  • 7 Wang Q. Luo J. Cao Y. Zhang L. Li C. Yuan Q. Faming Zhuanli Shenqing Gongkai Shuomingshu Patent CN105367455, 2016
  • 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
  • 9 Zhao T. Grützke M. Götz KH. Druzhenkob T. Huhn T. Dalton Trans. 2015; 44: 16475
  • 10 Liu Y. Zhang Z. Faming Zhuanli Shenqing Gongkai Shuomingshu Patent CN1454892, 2003
  • 11 Bao X. Song D. Qiao X. Zhao X. Chen G. Org. Process Res. Dev. 2016; 20: 1482
  • 12 Wolfson A. Shokin O. Tavor D. J. Mol. Catal. A: Chem. 2005; 226: 69
  • 13 Lu J. Ma H. Han B. Lu B. Bao X. Faming Zhuanli Shenqing Gongkai Shuomingshu Patent CN 102633696 A, 2012
  • 15 Weston AW. Suter CM. Org. Synth. 1941; 21: 27
  • 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
  • 18 Marzolph G. Blank HU. Ger. Offen DE 3016186, 1981