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1.
Chem Asian J ; 19(11): e202400116, 2024 Jun 03.
Article in English | MEDLINE | ID: mdl-38584137

ABSTRACT

(C-X) bonds (X=C, N, O) are the main backbone for making different skeleton in the organic synthetic transformations. Among all the sustainable techniques, electro-organic synthesis for C-X bond formation is the advanced tool as it offers a greener and more cost-effective approach to chemical reactions by utilizing electrons as reagents. In this review, we want to explore the recent advancements in electrochemical C-O bond formation. The electrochemically driven C-O bond formation represents an emerging and exciting area of research. In this context, electrochemical techniques offers numerous advantages, including higher yields, cost-efficient production, and simplified work-up procedures. This method enables the continuous and consistent formation of C-O bonds in molecules, significantly enhancing overall reaction yields. Furthermore, both intramolecular and intermolecular C-O bond forming reaction provided valuable products of O-containing acyclic/cyclic analogue. Hence, carbonyl (C=O), ether -O-), and ester (-COOR) functionalization in both cyclic/acyclic analogues have been prepared continuously via this innovative pathway. In this context, we want to discuss one-decade electrochemical synthetic pathways of various C-O bond contains functional group in chronological manner. This review focused on all the synthetic aspects including mechanistic path and has also mentioned overall critical finding regarding the C-O bond formation via electrochemical pathways.

2.
Chemistry ; 30(13): e202303287, 2024 Mar 01.
Article in English | MEDLINE | ID: mdl-37997510

ABSTRACT

An efficient and short synthesis of fused dihydroisoquinolines, diaryl substituted pyridine derivatives in good to high yields has been established by using an environmentally safe, solvent-metal-oxidant-free tandem approach. In this article, we discuss how the electrocyclic reaction is more pronounced in the solid phase in the presence of urea, whereas the typical aza-Michael addition is more prominent in presence of arylamine in the solution phase for 3-(2-formylcycloalkenyl)acrylic ester derivative substrates. The wide range of substrates and urea-promoted neat synthesis made our approach more significant in medical and also analytical science. Moreover, an isoquinoline alkaloid decumbenine B analogue has been synthesized by using our newly developed neat methodology. We have also investigated the photophysical properties of the synthesized fused dihydroisoquinoline derivatives. One of the synthesized molecules was used as a sensor for the selective detection of toxic picric acid. Therefore, the effective neat synthesis and molecular sensing applications of these compounds made our approach more exciting in the field of heterocyclic chemistry.

3.
J Org Chem ; 88(9): 5622-5638, 2023 May 05.
Article in English | MEDLINE | ID: mdl-36996425

ABSTRACT

Herein, we have presented a weak acid-promoted tandem aza-Michael-aldol strategy for the synthesis of diversely fused pyrrolo[1,2-a]quinoline (tricyclic to pentacyclic scaffolds) by the construction of both pyrrole and quinoline ring in one pot. The described protocol fabricated two C-N bonds and one C-C bond in the pyrrole-quinoline rings which have been sequentially formed under transition-metal-free conditions by the extrusion of eco-friendly water molecules. A ketorolac drug analogue has been synthesized following the current protocol, and one of the synthesized tricyclic pyrrolo[1,2-a]quinoline fluorophores has been used to detect highly toxic picric acid via the fluorescence quenching effect.

4.
Org Lett ; 10(21): 4795-7, 2008 Nov 06.
Article in English | MEDLINE | ID: mdl-18828592

ABSTRACT

A novel methodology for the synthesis of 9,10-dihydrophenanthrene and its analogues has been developed via a palladium-assisted 6pi electrocyclic reaction followed by formaldehyde elimination.

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