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Synthesis 2017; 49(13): 2971-2979
DOI: 10.1055/s-0036-1588992
DOI: 10.1055/s-0036-1588992
paper
Targeted Synthesis of 4-Chloro-3-formylthieno[2,3-b]pyridine and/or 4-Chlorothieno[2,3-b]pyridine by Reaction between N-Protected 3-Acetyl-2-aminothiophenes and Vilsmeier–Haack Reagent
Further Information
Publication History
Received: 01 February 2017
Accepted after revision: 13 March 2017
Publication Date:
07 April 2017 (online)
Abstract
Formylated chlorothieno[2,3-b]pyridine derivatives were synthesized by reaction between N-protected 3-acetyl-2-aminothiophenes and Vilsmeier–Haack reagent under classical conditions. These products were not accessible without N-protection of the starting materials or by reaction between the reagent and 4-chlorothieno[2,3-b]pyridine under any conditions. The conditions of the reaction could be altered to produce unformylated derivatives in better yields than reaction with unprotected aminothiophene.
Key words
thiophenes - Vilsmeier–Haack - thieno[2,3-b]pyridine - chlorination - chloroformylation - cyclizationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588992.
- Supporting Information
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References
- 1 Davies DT. Forbes IT. Thompson M. WO9304068 (A1), 1993
- 2 Bakhite EA. Abdel-Rahman AE. Mohamed OS. Thabet EA. Bull. Korean Chem. Soc. 2002; 23: 1709
- 3a Yasuma T. Baba A. Makino H. Aoki I. Nagata T. WO 0164685, 2001
- 3b Madhusudana K. Shireesha B. Naidu VG. M. Ramakrishna S. Narsaiah B. Rao AR. Diwan PV. Eur. J. Pharmacol. 2012; 678: 48
- 4 Luiz CS. P. Borges JC. Santos MS. d. Ferreira VF. Bernardino AM. R. Tonioni R. Sathler PC. Castro HC. Santos DO. Nascimento SB. Bourguignon SC. Magalhães UO. Cabral LR. R. J. Microbiol. Antimicrob. 2012; 4: 32
- 5 Masch A. Kunick C. Biochim. Biophys. Acta, Proteins Proteomics 2015; 1854: 1644
- 6 Boschelli DH. Cole DC. Asselin M. Barrios SA. C. Wu B. Tumey LN. WO 2007038519, 2007
- 7 Vilsmeier A. Haack A. Ber. Dtsch. Chem. Ges. B 1927; 60: 119
- 8 Su W. Weng Y. Jiang L. Yang Y. Zhao L. Chen Z. Li Z. Li J. Org. Prep. Proced. Int. 2010; 42: 503
- 9a Harnisch H. Justus Liebigs Ann. Chem. 1973; 765: 8
- 9b Nohara A. Umetani T. Sanno Y. Tetrahedron Lett. 1973; 14: 1995
- 9c Seixas RS. G. R. Silva AM. S. Alkorta I. Elguero J. Monatsh. Chem. 2011; 142: 731
- 10 Meth-Cohn O. Narine B. Tetrahedron Lett. 1978; 19: 2045
- 11 Amaresh RR. Perumal PT. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1997; 36: 541
- 12 Abdelwahab A. Hanna A. Kirsch G. Synthesis 2016; 48: 2881
- 13 Furniss BS. Hannaford AJ. Smith PW. G. Tatchell AR. Vogel’s Textbook of Practical Organic Chemistry. 5th ed.; 1989: 1273
- 14 Hauptmann S. Weißenfels M. Scholz M. Werner E.-M. Köhler H.-J. Weisflog J. Tetrahedron Lett. 1968; 9: 1317