An Aquatic Pseudo-Four-Component Reaction for the Synthesis of Highly Substituted Thiophenes

Abstract

A novel and simple procedure was developed for the construction of fully substituted thiophenes. A series of α-haloacetophenone derivatives were converted into fully substituted thiophenes by treatment with sodium sulfide in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene and sodium iodide in aqueous ethanol under aerobic conditions. A mechanism for the reaction is proposed.

Key words

sulfur - heterocycles - alkyl halides - coupling - dehydrogenation - multicomponent reactions

• References

• 1a Medower C, Wen L, Johnson WW. Chem. Res. Toxicol. 2008; 21: 1570
• 1b Koike K, Jia Z, Nikaida T, Liu Y, Guo D. Org. Lett. 1999; 1: 197
• 2a Jang S.-Y, Sotzing GA, Marquez M. Macromolecules 2004; 37: 4351
• 2b Brown JW, Lambe GJ, Foot PJ. S, Clipson JA. Macromol. Rapid Commun. 2004; 25: 1000
• 3a Noda T, Imae I, Noma N, Shirota Y. Adv. Mater. (Weinheim, Ger.) 1997; 9: 239
• 3b Noda T, Ogawa H, Noma N, Shirota Y. Adv. Mater. (Weinheim, Ger.) 1997; 9: 720
• 4 Jarvest RL, Pinto IL, Ashman SM, Dabrowski GE, Fernandez AV, Jennings LG, Lavery P, Tew DG. Bioorg. Med. Chem. Lett. 1999; 9: 443
• 5 Gewald K, Schinke E, Böttcher H. Chem. Ber. 1966; 99: 94
• 6a Hinsberg O. Ber. Dtsch. Chem. Ges. 1910; 43: 901
• 6b Wynberg H, Zwanenburg DJ. J. Org. Chem. 1964; 29: 1919
• 6c Wynberg H, Kooreman HJ. J. Am. Chem. Soc. 1965; 87: 1739
• 6d Birch A, Crombie DA. Chem. Ind. (London) 1971; 177
• 7a Matloubi Moghaddam F, Zali Boeini H. Tetrahedron Lett. 2003; 44: 6253
• 7b Mohan C, Kumar V, Mahajan MP. Tetrahedron Lett. 2004; 45: 6075
• 7c Majumdar KC, Ghosh M, Jana M, Saha D. Tetrahedron Lett. 2002; 43: 2111
• 8 Matloubi Moghaddam F, Zali Boeini H. Tetrahedron 2004; 60: 6085
• 9 Compounds 2c, 2i, and 2k have been reported, see: Yuji M, Inazu T, Yoshino T. Bull. Chem. Soc. Jpn. 1980; 53: 1187