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Synthesis of 1,2,3‐Trisubstituted Cyclopentannulated Benzothiophenes through an Acid‐Mediated, Solvent‐Free, One‐Pot Domino Process
Author(s) -
Satpathi Bishnupada,
Dhiman Seema,
Ramasastry S. S. V.
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201400008
Subject(s) - chemistry , intramolecular force , domino , aldol reaction , structural isomer , molecular electronics , brønsted–lowry acid–base theory , combinatorial chemistry , solvent , organic chemistry , molecule , computational chemistry , catalysis
Abstract The synthesis of 1,2,3‐trisubstituted cyclopenta[ b ]thiophenes was achieved through a Brønsted acid mediated domino process under solvent‐free conditions. In this one‐pot process, benzothienylation of 1,3‐dicarbonyls follows an intramolecular aldol‐type reaction leading to the generation of functionalized and highly substituted annulated benzothiophenes. This class of compounds find potential applications in molecular electronics and exhibit significant biological activities. A brief theoretical investigation established a significant relationship between the energy of the regioisomers and their distribution.