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-carbonitril es
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Titre | 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-carbonitril es |
Type de publication | Journal Article |
Year of Publication | 2019 |
Auteurs | Mkaouar K, Iriepa I, Diez-Iriepa D, Marco-Contelles J, Ismaili L, Chabchoub F |
Journal | CHEMISTRYSELECT |
Volume | 4 |
Pagination | 12902-12905 |
Date Published | NOV 28 |
Type of Article | Article |
ISSN | 2365-6549 |
Mots-clés | Cyanides, Density functional calculations, Diastereoselectivity, formic acid, Oxygen heterocycles |
Résumé | The 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-carbonitril es (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. |
DOI | 10.1002/slct.201903982 |