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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

1,2
, 2
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 and 1,*
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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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