Efficient synthesis of 3-benzoyl Benzo[b]thiophenes and raloxifene via Mercury(II)-Catalyzed cyclization of 2-alkynylphenyl alkyl sulfoxides
| Autor: | Shi-Ming Wen, Chin-Chau Chen, Ming-Jung Wu, Cheng-Han Lin |
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| Rok vydání: | 2018 |
| Předmět: |
chemistry.chemical_classification
010405 organic chemistry Aryl Organic Chemistry Sonogashira coupling Sulfoxide Alkylation 010402 general chemistry 01 natural sciences Biochemistry Medicinal chemistry Coupling reaction 0104 chemical sciences Catalysis chemistry.chemical_compound chemistry Drug Discovery Alkyl Demethylation |
| Zdroj: | Tetrahedron. 74:2493-2499 |
| ISSN: | 0040-4020 |
| DOI: | 10.1016/j.tet.2018.03.067 |
| Popis: | The unique selective estrogen receptor modulator, Raloxifene (1), and antitubulin agent 2 were synthesized through the key intermediate, 4-methoxybenzyl 2-bromo-4-methoxyphenyl sulfoxide (6), respectively. It was found that compared with the o-sulfanyl aryl bromides, the sulfinyl group at ortho position accelerated the Sonogashira coupling reaction of aryl bromides. Thus, compound 6 was coupled with 3,4,5-trimethoxyphenyl acetylene, followed by mercury-catalyzed cyclization reaction afford compound 2 in 79% overall yield. Raloxifene (1) was prepared from compound 6 in four steps and 33% overall yield via coupling reaction with 1-trimethylsily-2-(4-tert-butyldimethylsiloxy)phenylethyne, mercury-catalyzed cyclization reaction, alkylation and demethylation. |
| Databáze: | OpenAIRE |
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