CINDECA   05422
CENTRO DE INVESTIGACION Y DESARROLLO EN CIENCIAS APLICADAS "DR. JORGE J. RONCO"
Unidad Ejecutora - UE
artículos
Título:
Unexpected Result in the Catalytic Solvent-free Multicomponent Synthesis of 2-Amino-3-cyano-4 H -chromene
Autor/es:
RIVERA, TOA S.; PALERMO, VALERIA; PIZZIO, LUIS R.; SOSA, ALEXIS A.; ROMANELLI, GUSTAVO P.
Revista:
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL
Editorial:
ROUTLEDGE JOURNALS, TAYLOR & FRANCIS LTD
Referencias:
Año: 2019 p. 1 - 13
ISSN:
0030-4948
Resumen:
Multicomponent reactions (MCRs) are efficient and effective methods for the sustainable and diversity-oriented synthesis of heterocycles.1,2 In a green chemistry context,the traditional methods of performing chemical synthesis are unsustainable, and MCRsprovide an important solution since they are more efficient, cost-effective, and lesswasteful. A known MCR for example is the condensation between aldehyde, malononitrile, and phenol or naphthol to give 2-amino-3-cyano-4H-chromenes.3In this regard, heteropolyacids and derivatives represent one of the most importantcategories of solid catalysts. They are widely utilized due to their acid and redox properties and represent an important family of materials used under heterogeneous andsolvent-free conditions for the synthesis of different heterocycles.4 Keggin, WellsDawson and Preyssler heteropolyacid composites are used in heterocyclic synthesis ascatalysts in several MCRs for the preparation of dihydropyrimidinones,5 quinazolinones,6 pyridines,7 xanthenones,8 imidazoles,9 pyrazoles,10 and 1,4-dihydropyridines.11Recently, some applications related to the use of zirconia/heteropolyacid composites ingreen organic synthesis and relevant technological procedures have been reported.These include veratrole benzoylation,12 oleochemistry transesterification and esterification reactions,13 biomass valorization through the esterification of 2-furoic acid withalcohols,14 synthesis of bioadditives for biofuels from glycerol esterification with aceticacid,15 and synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes16 and quinoxalines.17Moreover, in the last decade, great attention has been paid to 2-amino-3-cyano-4Hchromenes due to their antimicrobial, antifungal, antioxidant, and pro-apoptotic activities.18,19 The classical method for their synthesis involves the MCR among aldehydes,malononitrile, and phenol or naphthol in the presence of a catalyst, such as NaOH,20Na2CO3,21 Al2O3,22 methanesulfonic acid,3 or heteropolyacid.23