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Title

Synthesis of (±)-cis-1-Aryl-3-oxo-2,3-dihydro-1H-benzo[f]chromene-2-carbonitriles and (±)-trans-4-Aryl-2-oxo-3,4-dihydro-2H-benzo[h]chromene-3-carbonitriles

AuthorsMkaouar, K.; Iriepa, I.; Diez-Iriepa, Daniel; Marco-Contelles, José ; Ismaili, L.; Chabchoub, F.
KeywordsCyanides
Density functional calculations
Diastereoselectivity
Formic acid
Oxygen heterocycles
Issue Date2019
PublisherWiley-VCH
CitationChemistrySelect 4: 12902-12905 (2019)
AbstractThe unexpected stereospecific synthesis of (±)-cis-1-aryl-3-oxo-2,3-dihydro-1H-benzo[f]chromene-2-carbonitriles (2) and (±)-trans-4-aryl-2-oxo-3,4-dihydro-2H-benzo[h]chromene-3-carbonitriles (4) from (±)-3-amino-1-aryl-1H-benzo[f]chromene-2-carbonitriles (1) and (±)-2-amino-4-aryl-4H-benzo[h]chromene-3-carbonitriles (3), respectively, by reacting them in formic acid (88%), at reflux, is reported. A DFT analysis has been applied with success to justify these highly stereospecific reactions.
Publisher version (URL)http://dx.doi.org/10.1002/slct.201903982
URIhttp://hdl.handle.net/10261/203073
DOI10.1002/slct.201903982
Identifiersdoi: 10.1002/slct.201903982
issn: 2365-6549
Appears in Collections:(IQOG) Artículos
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