Spiro Cyclohexadienones from the Reaction of Phenolic Enaminone Derivatives with Hypervalent Iodine Reagents 英文参考文献.docVIP

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Spiro Cyclohexadienones from the Reaction of Phenolic Enaminone Derivatives with Hypervalent Iodine Reagents 英文参考文献.doc

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Spiro Cyclohexadienones from the Reaction of Phenolic Enaminone Derivatives with Hypervalent Iodine Reagents 英文参考文献

Molecules 2000, 5, 874-879 molecules ISSN 1420-3049 Spiro Cyclohexadienones from the Reaction of Phenolic Enaminone Derivatives with Hypervalent Iodine Reagents Anna Asmanidou, Ioannis Papoutsis, Spyros Spyroudis* and Anastasios Varvoglis Laboratory of Organic Chemistry, Chemistry Department, University of Thessaloniki, Thessaloniki 54006, Greece Tel.: 003031-997833, Fax: 003031-997679, E-mail: sspyr@chem.auth.gr Received: 6 May 2000 / Accepted: 25 May 2000 / Published: 9 June 2000 Abstract: Phenolic enamino compounds, prepared from 2-(4-hydroxyphenyl)-ethylamine and the corresponding -keto carbonyl compounds, afford spiro cyclohexadienone deriva- tives on reaction with hypervalent iodine reagents. Keywords: Spiro cyclohexadienones, hypervalent iodine, enamino esters. Introduction The action of hypervalent iodine compounds on phenols gives rise to a variety of products depen- ding on the nature of the phenol and the reaction conditions. The most interesting reaction pathway is oxidation of the phenolic moiety with simultaneous nucleophilic attack on the para position of the phenolic ring. When this attack occurs place intramolecularly, a variety of spirodienone derivatives are formed with considerable synthetic possibilities [1-3]. Especially noteworthy is the oxidative coupling of phenolic derivatives of -phenylethylamine, studied extensively by Kita and coworkers [4]. This coupling, outlined below, offers an easy access to pharmacologically interesting natural products, when the substituent on nitrogen is an aromatic or a quinone ring. ? 2000 by MDPI (). Reproduction is permitted for noncommercial purposes. 875 Molecules 2000, 5 O OH I (III) NH N H Figure 1. Results and Discussion Continuing the exploration of the chemistry of hypervalent iodine reagents [5], we investigated the possibility of analogous cyclization reactions using enamino carbonyl systems of type I. Recently we reported the isolation of