3- arylacrylates

Perkin condensation is the reaction between aromatic aldehydes and aliphatic acid anhydrides (in the presence of the sodium salt) to form 3-arylacrylic acid... 

Arylacetic acids, synthesis of, 1, 2 22, 4 3-Arylacrylic acids, synthesis of, 1, 8... 

A general route to aryl-substituted pyruvic acids (e.g. phenylpyruvic acid, Expt 5.175) is the acid hydrolysis of 2-acetamido-3-arylacrylic acids (19), which are themselves formed by hydrolysis of the corresponding azlactones (18) (cf. Expt 8.21) with water. 

Table 1 The Rh(/ -SpirOP) -catalyzed asymmetric hydrogenation of (Z)-2-acetamido-3-arylacrylic acids ...

Further studies for the hydrogenation of other prochiral ami-doacrylic acids confirmed that the high enantioselectivity of the catalyst is quite general. Several (Z)-2-acetamido-3-arylacrylic acids were hydrogenated with this catalyst and in all cases the desired products were found to have ee values of over 97%. More detailed data are summarized in Table 1. 

Kekule70 recommended zinc and alkali hydroxide solutions for preparation of the so-called nascent hydrogen . Somewhat similarly, Raney nickel alloys in aqueous alkali have been used repeatedly for reductions. The aluminium that goes into solution in these reactions reduces naphthalene and its substitution products,71 cyclooctatetraene,72 and in particular 3-arylacrylic adds73 in good yield. 

Keywords 2-Azido-3-arylacrylates, terminal alkenes, dichloromethane, palladium acetate, tri-fluoroacetic acid (TEA), oxygen-atmosphere, room temperature, domino reaction, intramolecular cyclization followed by olefination, 3-alkenyl indoles... 

A mixture of 2-azido-3-arylacrylate (1 0.3 mmol), terminal alkene (2 0.9 mmol), Pd(OAc)2 (0.03 mmol), TFA (2.4 mmol) was stirred in anhydrous dichloromethne (3 mL) under oxygen atmosphere at room temperature for 8 h. The reaction mixture was quenched with water (10 mL) and then extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated under vacuum. The concentrated crude residue was purified by column chromatography using petrol ether-ethyl acetate mixture as eluent to furnish 3-alkenyl indoles 3 with 55-83% yield. All the products were are characterized by detailed spectral studies. 

Zhang, Y., Liu, S., Yu, W., Hu, M., Zhang, G., and Yu, Y. (2013). Palladium-catalyzed S5mthesis of 3-aUcenyl indoles from 2-azido-3-arylacrylates and terminal alkenes at room temperature. Tetrahedron, 69, 2070-2074. 

Yang YY, Shou WG, Chen ZB, Hong D, Wang YG (2008) A tandem approach to isoquinolines from 2-azido-3-arylacrylates and a-diazocarbonyl compounds. J Org Chem 73 3928-3930... 

Nam, N. Ngoc, N. A. Zun, A. B. Synthesis of (6,7-dimethoxy-2-oxo-2H-chromen-4-yl)methyl 3-arylacrylates as water soluble antitumor agents. Lett. Drug Des. Discov. 2011,8,312-316. 

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