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Molecules 2011, 16(1), 384-402; doi:10.3390/molecules16010384
Article

Functionalized 4-Hydroxy Coumarins: Novel Synthesis, Crystal Structure and DFT Calculations

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1 Laboratory of Inorganic Chemistry, Department of Chemistry, University of Athens, Panepistimiopolis, Athens 15771, Greece 2 Laboratory of Organic Chemistry, School of Chemical Engineering, National Technical University of Athens, Zografou Campus, Athens 15773, Greece 3 Chemistry Department, University of Loughborough, Leicestershire, LE113TU, UK
* Author to whom correspondence should be addressed.
Received: 22 November 2010 / Revised: 20 December 2010 / Accepted: 27 December 2010 / Published: 7 January 2011
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Abstract

A novel short-step methodology for the synthesis in good yields of functionalized coumarins has been developed starting from an activated precursor, the N-hydroxysuccinimide ester of O-acetylsalicylic acid. The procedure is based on a tandem C-acylation-cyclization process under mild reaction conditions. The structure of 3-methoxycarbonyl-4-hydroxy coumarin has been established by X-ray diffraction analysis and its geometry was compared with optimized parameters by means of DFT calculations.
Keywords: coumarins; N-hydrocysuccinimide ester; C-acylation; β,β΄-dicarbonyl system; cyclization; DFT coumarins; N-hydrocysuccinimide ester; C-acylation; β,β΄-dicarbonyl system; cyclization; DFT
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Stefanou, V.; Matiadis, D.; Melagraki, G.; Afantitis, A.; Athanasellis, G.; Igglessi-Markopoulou, O.; McKee, V.; Markopoulos, J. Functionalized 4-Hydroxy Coumarins: Novel Synthesis, Crystal Structure and DFT Calculations. Molecules 2011, 16, 384-402.

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