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  • Title: Efficient one-pot synthesis of highly substituted thiophene library from 1,3-dicarbonyl compounds.
    Author: Wang Y, Huang J, Chai Y, Liu Q, Liang Y, Dong D.
    Journal: J Comb Chem; 2008; 10(4):511-6. PubMed ID: 18491943.
    Abstract:
    A facile and efficient one-pot synthesis of highly substituted thiophenes has been developed and employed for the preparation of a small focused library. Treatment of 1,3-dicarbonyl compounds 1 with CS2 in the presence of K2CO3 in DMF at room temperature, followed by stepwise addition of alkyl bromides 2 and methylene active bromides 3, provided via intramolecular cyclization 2,3,4,5-tetrasubstituted thiophenes 4 in yields of 77-94%. This protocol, combining construction and modification of the thiophene ring, increases the structural diversity of final products from readily available materials. A mechanism for the one-pot synthesis of thiophenes of type 4 has been proposed. A small focused library of thiophenes is prepared using the sequential addition of reagents to achieve unique substitution in the 2 and 5 position of the thiophene ring.
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