Allan-Robinson Reaction

Synthesis of flavones or isoflavones by the treatment of of o-hydroxyaryl ketones with aromatic aldehydes. Cf. Kostanecki reaction on page 322. 

Name Reactions, 4th ed., DOI 10.1007/978-3-642-01053-8 4 Springer-Verlag Berlin Heidelberg 2009 

Tsukayama, M. Kawamura, Y. Yamamoto, S. Chem. Pharm. Bull. 1987, 35,4465 472. 

One-carbon homologation of carboxylic acids using diazomethane. 

Name Reactions A Collection of Detailed Mechanisms and Synthetic Applications, DOI 10.1007/978-3-319-03979-4 4, Springer International Publishing Switzerland 2014 

Bagchi, D. Pakrashi, S. C. Indian J. Chem., Sect. B1982,2IB, 1037. 

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Although the literature refers to the formation of chromones/coumarins as the Kostanecki reaction (and often the Kostanecki-Robinson reaction) and the synthesis of flavones as the Allan-Robinson reaction, others have chosen to merge the two reactions and refer to both transformations as the Kostanecki-Robinson reaction. This section will follow the latter school of thought, and use the Kostanecki-Robinson (K-R) nomenclature. 

Also known as Kostanecki-Robinson reaction. Transformation 1 2 represents an Allan—Robinson reaction (see page 8), whereas 1 3 is a Kostanecki (acylation) reaction ... 

Allan-Robinson reaction. Preparation of fla-vones or isoflavones by condensing o-hydroxyaryl ketones with anhydrides of aromatic acids and their sodium salts. 

This reaction was first reported by Allan and Robinson in 1924. It is the synthesis of fiavones or isoflavones derivatives by means of the condensation between o-hydroxyaryl ketones and an anhydride of aromatic acid in the presence of the sodium salt of corresponding acid in the anhydride. Thus this reaction is known as the Allan-Robinson condensation, Allan-Robinson s flavone synthesis, Allan-Robinson reaction, and Allan-Robinson synthesis. ... 

Algar-Flynn-Oyamada Reaction Allan-Robinson Reaction Allvlic Rearrangements Aluminum Alkoxide Reduction... 

Gripenberg in The Chemistry ofFlavonoid Compounds, Geissman, Ed. (New York, 1962) p 410. Mechanistic studies K. Bowden, M. Chehel-Amiran, J. Chem. Soc. Perkin Trans. II 1986, 2039. Synthetic applications P. K. Jain etal, Synthesis 1982, 221 J. Zhu etal., Chem. Commun. 1988,1549 A. V. Kalinin et al, Tetrahedron Letters 39,4995 (1998) D. C. G. Pinto et al, New J. Chem. 24, 85 (2000). Cf. Allan-Robinson Reaction Kostanecki Acylation. 

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