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Synthesis of Phenanthrene Derivatives through the Reaction of an α , α ‐Dicyanoolefin with α , β ‐Unsaturated Carbonyl Compounds
Author(s) -
Alizadeh Abdolali,
Hosseini Seyed Yasub,
Sedighian Hadi,
Bayat Fahimeh
Publication year - 2015
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201500120
Subject(s) - chemistry , phenanthrene , aldehyde , ninhydrin , wittig reaction , catalysis , condensation reaction , organic chemistry , condensation , reaction mechanism , medicinal chemistry , amino acid , physics , thermodynamics , biochemistry
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, 1 H‐ and 13 C‐NMR, and EI‐MS). A plausible mechanism for this type of reaction is proposed ( Scheme 1 ).