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Synthesis 2016; 48(15): 2429-2437
DOI: 10.1055/s-0035-1561428
DOI: 10.1055/s-0035-1561428
paper
The Synthesis of Two Regioisomeric Aldehydes with a Tetrahydrobenzo[b]thiophene Scaffold and Their Application in Solvent-Free Intramolecular 1,3-Dipolar Cycloaddition Reactions
Further Information
Publication History
Received: 12 February 2016
Accepted after revision: 07 March 2016
Publication Date:
26 April 2016 (online)
Abstract
The paper describes the synthesis of two regioisomeric 2-amino-3-formyl- and 3-amino-2-formyl-substituted derivatives of tetrahydrobenzo[b]thiophene and their subsequent thermally initiated reactions with secondary amines to give azomethine ylides that undergo intramolecular 1,3-dipolar cycloadditions. In this way, two series of new fused heterocyclic compounds with three stereogenic centers were prepared. The compounds were identified and their structures were determined.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561428.
- Supporting Information
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References
- 1 Magd-El-Din AA, Atta SM. Sh, Abd-El-All AS, Galal SA, Abdalah MA. World J. Chem. 2009; 4: 112 ; http://www.idosi.org/wjc/4(2)09/4.pdf
- 2 Soliman R, Habib NS, El-Tombary AA, El-Hawash SA. M, Shaaban OG. Sci. Pharm. 2009; 77: 755 ; DOI: 10.3797/scipharm.0904-17
- 3 Mishra K. Int. Arch. Appl. Sci. Technol. 2014; 5: 70 ; http://www.soeagra.com/iaast/iaastmarch2014/5.pdf
- 4 Wang S.-B, Liu D.-C, Deng X.-Q, Gong G.-H, Quan Z.-S. Lat. Am. J. Pharm. 2014; 33: 1061
- 5 Gajjar KA, Gajjar AK. IN 1124MU2013, 2015
- 6 Gryshenko AA, Bdzhola VG, Balanda AO, Briukhovetska NV, Kotey IM, Golub AG, Ruban TP, Lukash LL, Yarmoluk SM. Bioorg. Med. Chem. 2015; 23: 2287
- 7 Ye F, Chen D, Yu S, Wang Y, Wang Y, Chen L, Song X, Xie Z, Liang G, Li X, Liu Z, Lin D. CN 105017277, 2015
- 8 Edwards JP, Neff DK, Smith DM, Venable JD. US 20090075970, 2009 ; Chem. Abstr. 2009, 150, 329838
- 9 Butini S, Fattorusso C, Gemma S, Sanna Coccone S, Borriello M. WO 2008031888, 2008
- 10a Kim B.-K, Lee S.-S, Shin C.-J, Jung S.-H, Kwon O.-H, Kim Y.-K, Kim C.-W, Kim H.-S, Seo J.-H, Yu E.-S, Choi BK, Hwang KY. WO 2015105313, 2015
- 10b Kim B.-K, Jung H.-K, Han S.-J, Kwon O.-H, Kim Y.-K, Kim C.-W, Kim H.-S, Seo J.-H, Shin C.-J, Yu E.-S, Choi BK, Hwang KY. WO 2015105315, 2016
- 11a Huisgen R In 1,3-Dipolar Cycloaddition Chemistry . Vol. 1. Padwa A. Wiley; New York: 1984
- 11b Padwa A. Angew. Chem., Int. Ed. Engl. 1976; 15: 123
- 11c Harwood L, Vickers RJ In Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products. . Padwa A, Pearson WH. Wiley; New York: 2003. Chap. 3, 169
- 12 Pospíšil J, Potáček M. Eur. J. Org. Chem. 2004; 710
- 13 Pospíšil J, Potáček M. Tetrahedron 2007; 63: 337
- 14 Pospíšil J, Potáček M. Heterocycles 2004; 63: 1165
- 15 Neuschl M, Bogdal D, Potáček M. Molecules 2007; 12: 49
- 16 Gewald K, Schinke E, Böttcher H. Chem. Ber. 1966; 99: 94
- 17 Tenora L, Buchlovič M, Man S, Potáček M. Tetrahedron Lett. 2011; 52: 401
- 18 Kuehne ME. J. Am. Chem. Soc. 1959; 81: 5400
- 19 Armarego WL. F, Perin DD. Purification of Laboratory Chemicals, Butterworth-Heinemann: Oxford, 2000 . 4th ed;
- 20 CCDC 1436220 (A6b), 1436221 (A6c), 1436222 (B6b), and 1436223 (B6c) contain the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
- 21 SHELXTL, Version 5.10. Bruker AXS; Madison (WI, USA): 1997