Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2017; 49(14): 3165-3170
DOI: 10.1055/s-0036-1589015
DOI: 10.1055/s-0036-1589015
paper
Synthesis of 3-Formylbenzenesulfonyl Chloride Derivatives
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.
Key words
3-formylbenzenesulfonyl chloride - aldehyde sodium bisulfite - chlorosulfonation - two-stage reaction - chemical derivatization methodSupporting Information
- Supporting information for this article is available online at https://doi.org /10.1055/s-0036-1589015.
- Supporting Information
Primary Data
- 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.
-
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
- 14a Faul M. Larsen R. Levinson A. Tedrow J. Vounatsos F. J. Org. Chem. 2013; 78: 1655
- 14b Knight CJ. Millan DS. Moses IB. Robin AA. Selby MD. Org. Process Res. Dev. 2012; 16: 697
- 15 Weston AW. Suter CM. Org. Synth. 1941; 21: 27
- 16a Frost CG. Hartley JP. Griffin D. Synlett 2002; 1928
- 16b Hawley’s Condensed Chemical Dictionary . 13th ed.; Lewis RJ. Sr. Wiley; New York: 1997: 1113
- 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