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1.
J Org Chem ; 87(15): 9755-9763, 2022 08 05.
Artigo em Inglês | MEDLINE | ID: mdl-35839324

RESUMO

An iron-catalyst mediated one-pot multicomponent route for the synthesis of novel 6-thioxo-hexahydroindeno[1',2':4,5]imidazo[1,5-a]pyridin-12(6H)-one scaffolds has been developed using ninhydrin, l-proline, and aryl isothiocyanates in ethanol medium. This methodology offers an interesting [1,2] oxygen shift mechanism pathway via a number of ring-opening and ring-closing cascade steps to provide diverse substituted hexahydroindeno-imidazo[1,5-a]pyridinones in excellent to good yields. The stereochemistry of the proline ring is lost during the course of the reaction. This protocol is well acceptable toward both electron-accepting and electron-donating functionalities at the ortho-, meta-, and para-positions of the isothiocyanate moiety. Nonhazardous conditions, step economic, and easy operational process are the advantages of this methodology.


Assuntos
Oxigênio , Piridonas , Catálise , Estrutura Molecular
2.
Mol Divers ; 26(5): 2561-2573, 2022 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-34978012

RESUMO

Herein, we successfully developed an easy access to bicycloacenaphtho[1,2-d]imidazole-8-thione by one-pot three-component MCRs of acenaphthoquinone, aryl or alkyl isothiocyanates and amines using environmentally benevolent and recyclable spinel NiFe2O4 nanocatalyst in aqueous ethanol. A broad number of products have been synthesized with both EDGs and EWGs present in the ring which increases the diversity of the protocol. The NiFe2O4 nanopowder has been synthesized and thoroughly characterized by powdered XRD, HRTEM, EDX, BET and ICP-AES analysis. The protocol to this bicyclic-heterocycle is noteworthy due to good to excellent yields, practical simplicity and high regioselectivity without any troublesome or hazardous by-products and its easy recovery and reusability of the catalyst. Spinel NiFe2O4 NPs-catalysed synthesis of various bicycloacenaphtho[1,2-d]imidazole-8-thione scaffolds under mild and sustainable conditions.


Assuntos
Nanopartículas , Tionas , Óxido de Alumínio , Aminas , Catálise , Etanol , Compostos Férricos , Imidazóis , Isotiocianatos , Óxido de Magnésio , Nanopartículas Metálicas , Níquel
3.
Beilstein J Org Chem ; 18: 133-142, 2022.
Artigo em Inglês | MEDLINE | ID: mdl-35140814

RESUMO

A heterogeneous and magnetically recyclable Ni-chitosan nanocatalyst was synthesized and thoroughly characterized by powder Fourier-transform infrared (FTIR) spectroscopy, X-ray diffraction (XRD) analysis, scanning electron microscopy (SEM), high-resolution transmission electron microscopy (HRTEM), energy-dispersive X-ray (EDX) spectroscopy, etc. It was effectively utilized in the eco-friendly synthesis of new C5-C6-unsubstituted 1,4-DHPs under ultrasonic irradiation. The important focus of the methodology was to develop an environmentally friendly protocol with a short reaction time and a simple reaction procedure. The other advantages of this protocol are a wide substrate scope, a very good product yield, the use of an eco-friendly solvent and a recyclable nanocatalyst, as well as reaction at room temperature.

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