A Consecutive Four‐Component Synthesis of Polysubstituted Thiophenes in Aqueous Medium. Issue 23 (14th June 2018)

• Record Type: Journal Article
• Authors: Adib, Mehdi; Rajai‐Daryasarei, Saideh; Pashazadeh, Rahim; Jahani, Mehdi; Yazzaf, Rozita; Amanlou, Massoud
• Is Part Of: European journal of organic chemistry. Issue 23(2018)
• Page Start: 3001
• Page End: 3016
• Publication Date: 2018-06-14
• Subjects: Multicomponent reactions -- Fused‐ring systems -- Sulfur heterocycles -- Green chemistry -- Consecutive reactions; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201800361
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : An efficient and straightforward four‐component synthesis of mono‐, bi‐ and tricyclic thiophenes from C–C + C + C + S atom fragments from 1, 3‐dicarbonyl compounds, aldehydes, activated methylene halides and elemental sulfur in aqueous medium is described. Arylidene‐1, 3‐dicarbonyls, N ‐phenacylpyridinium bromides/ N ‐( p ‐nitrobenzyl)pyridinium chloride, pyridinium ylides and 2, 3‐dihydrofurans are believed to be the key intermediates of these consecutive transformations. This synthetic strategy provides a potential route to the construction of a library of highly substituted thiophenes with a large substrate scope in good‐to‐excellent yields. Abstract : An efficient and straightforward four‐component domino synthesis of mono‐, bi‐ and tricyclic thiophenes from 1, 3‐dicarbonyl compounds, aldehydes, activated methylene halides and elemental sulfur in aqueous medium is described.