Annulation of Ethyl [Bis(ethylthio)methyl]benzoate and Ethyl 2-[1, 3]Dithiolan-2-yl-benzoate with α, β-Unsaturated Carbonyl Compounds : A New Synthesis of Naphthalene and Anthracene Derivatives

• Published in: Chemical & pharmaceutical bulletin Vol. 44; no. 10; pp. 1785 - 1789
• Main Authors: OZAKI, Yutaka, IMAIZUMI, Kazuhiro, OKAMURA, Kyouko, MOROZUMI, Masahiro, HOSOYA, Ayako, KIM, Sang-Won
• Format: Journal Article
• Language: English
• Published: TOKYO The Pharmaceutical Society of Japan 15.10.1996; Pharmaceutical Soc Japan; Maruzen
• Subjects: [2C+4C] annulation; anthracene; Chemistry; Chemistry, Medicinal; Chemistry, Multidisciplinary; Condensed benzenic and aromatic compounds; Exact sciences and technology; Life Sciences & Biomedicine; naphthalene; Organic chemistry; Pharmacology & Pharmacy; Physical Sciences; Preparations and properties; Science & Technology; synthesis; tandem Michael-Claisen condensation; anthracene; tandem Michael-Claisen condensation; synthesis; naphthalene; [2C+4C] annulation; ANNELATION; CONGENERS; Michael addition; Claisen condensation; Tricyclic compound; Tandem reaction; Anthracene derivatives; Condensed benzenic compound; Naphthalene derivatives; Organic sulfide; Annelation; Dithioacetal; Bicyclic compound; Phenols; Aromatic compound; Chemical synthesis
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.44.1785

Several kinds of fused cyclic compounds were obtained by tandem Michael-Claisen condensation of ethyl 2-[bis(ethylthio)methyl]benzoate and ethyl 2-[1, 3]dithiolan-2-yl-benzoate with α, β-unsaturated carbonyl compounds. Treatment of the annulated products with mercury(II)perchlorate trihydrate or N-chlorosuccinimide gave naphthoquinones, naphthalenes, and anthracenes.