Synthesis of Phenanthrene Derivatives through the Reaction of an α,α‐Dicyanoolefin with α,β‐Unsaturated Carbonyl Compounds |
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| Authors: | Abdolali Alizadeh Seyed Yasub Hosseini Hadi Sedighian Fahimeh Bayat |
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| Affiliation: | 1. Department of Chemistry, Tarbiat Modares University, P.O. Box 14115‐175, Tehran, Iran, (phone: +98‐21‐88006631;2. fax: +98‐21‐88006544) |
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| Abstract: | Phenanthrene derivatives were prepared by reacting an α,α‐dicyanoolefin with different α,β‐unsaturated carbonyl compounds resulting from Wittig reaction of ninhydrin and phosphanylidene or condensation of barbituric acid and an aldehyde. The easy procedure, mild and metal‐catalyst free, reaction conditions, good yields, and no need for chromatographic purifications are important features of this protocol. The structures of the product of type 3 and 5 were corroborated spectroscopically (IR, 1H‐ and 13C‐NMR, and EI‐MS). A plausible mechanism for this type of reaction is proposed (Scheme 1). |
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| Keywords: | Phenanthrene α ,α ‐Dicyanoolefin α ,β ‐Unsaturated carbonyl compounds Vinylogous addition Wittig reaction |
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