Abstract: This work represents a new synthesis of the antiepileptic drug rufinamide, through a one-pot multicomponent approach employing a Cu(I) as a catalyst. In this methodology, 2,6-difluoro benzyl bromide reacts with NaN3 and propiolamide in the presence of 0.5 mol% [Cu(phen)(PPh3)2]NO3 as a catalyst under click condition to afford regioselectively rufinamide in 95% yield. The new protocol offers several advantages such as high yields, clean reaction profile, short reaction time, use of less toxic catalyst, environmentally friendly and one pot approach. © 2017, Springer Science+Business Media Dordrecht.

Kaushik Chanda

Department of Chemistry

School of Advanced Sciences

Vellore Campus

Meena D.R

Rao R.N

Maiti B

Vellore Institute of Technology (VIT) is a private university located in&nbsp;Tamil Nadu, India. Founded in 1984, as Vellore Engineering College, the institution offers 20 undergraduate, 34 postgraduate, four integrated and four research programs. It has campuses in Vellore, Amravati, Bhopal and Chennai.

VIT is one of the top ranked private universities in India according to NIRF, THE and QS Rankings.&nbsp;Govt. of India has recognized&nbsp;VIT, Vellore as an&nbsp;Institution of Eminence. This has allowed VIT to take independent quality initiatives and move up in world ranking.

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VIT University

Research on Chemical Intermediates

In 2014, more than 80% of the marketed drugs in the US contained heterocyclic compounds, which play a major role in the drug-discovery process, as one of the primary components. Benzoxazole, consisting of an oxazole ring fused with a benzene ring, has shown profound impact in drug discovery research owing to its important bioactivity. This moiety has also shown important properties in material science. The synthesis of this privileged scaffold from readily available chemicals remains a primary focus for the synthetic chemistry community. In this review, efforts have been made to focus on the latest information available on the different synthetic strategies such as solution phase, multicomponent, green and solid phase chemistry and applications of different benzoxazole derivatives. Furthermore, the updated synthetic information incorporated in this review article will help to improve future synthesis of this scaffold. 1 Introduction 2 Solution-Phase Synthetic Approach to Substituted Benzoxazoles 2.1 Condensation of o-Aminophenol with Carboxylic Acids 2.2 Condensation of o-Aminophenol with Aldehydes 2.3 Condensation of o-Aminophenol with Orthoesters, ortho-Haloamides, or 1,1-Dihaloalkenes 2.4 Synthesis of Benzoxazoles from Schiff Bases 2.5 Miscellaneous 3 Multicomponent Synthetic Approach to Substituted Benzoxa­zoles 4 Solid-Phase Synthetic Approach to Substituted Benzoxazoles 5 Green Synthetic Approach to Substituted Benzoxazoles 5.1 Condensation of o-Aminophenol with Aldehydes 5.2 Condensation of o-Aminophenol with ortho-Substituted Benz­amides 5.3 Condensation of o-Aminophenol with Carboxylic Acid and its Derivatives 5.4 Condensation of o-Aminophenol with Alcohols or Amines 5.5 Miscellaneous 6 Bioactive Derivatives of Benzoxazoles 7 Conclusion and Outlook © Georg Thieme VerlagStuttgart · New York.

Synlett

A Decade Update on Benzoxazoles, a Privileged Scaffold in ­Synthetic Organic Chemistry

Benzimidazole and its derivatives are regarded as an important heterocyclic motif that exhibits a wide range of pharmaceutical applications including anticancers, antihypertensives, antivirals, antifungals, anti-HIVs, anti-convulsants, and anti-diabetics. In view of their wide ranging activities, the synthesis of benzimidazoles and its derivatives remain a primary focus for synthetic chemistry communities. Till date numerous reports especially on the synthesis of 2-arylbenzimidazoles have been published but lack of knowledge on the detailed synthetic reports of two important derivatives such as 2-aminobenzimidazoles, and 2-(alkyl/aryl)thio benzimidazoles still persists. However, owing to fast developing benzimidazole containing new drugs numerous reports have appeared on the synthesis of this privileged scaffold. In this review, efforts have been taken to shed light on the latest informations available on the syntheses and applications of different benzimidazole derivatives. We have also tried to summarize the chemistry involved in the synthesis of various derivatives of benzimidazole for medicinal applications. © 2017 Bentham Science Publishers.

Current Organic Synthesis

Synthesis and Medicinal Applications of Benzimidazoles: An Overview

A facile and efficient microwave assisted telescopic synthesis of diverse isoxazoles was reported in green reaction medium. Initially, N-hydroxyl imidoyl chlorides were reacted with substituted alkynes in aqueous medium using 2 mol% of [Cu(phen)(PPh3)2]NO3as catalyst to yield the 3,5-disubstituted isoxazoles. To improve the efficiency of the synthetic route for the regioselective synthesis of isoxazoles, commercially available aromatic aldehydes were converted to N-hydroxyl imidoyl chlorides followed by reaction with substituted alkynes in aqueous medium using Cu(I) as catalyst in telescopic manner. This telescopic new synthetic strategy facilitates the rapid generation of molecular frameworks in three-dimensional fashion leading to 3,5-disubstituted isoxazoles. This approach is visualized as an environmentally benign process and a simple operation to the privileged scaffolds. The present one-pot synthetic sequence allows the introduction of two points of structural diversity to expand chemical space with excellent purity and yields. © 2016 Elsevier Ltd

Tetrahedron Letters

Cu(I) catalyzed microwave assisted telescopic synthesis of 3,5-disubstituted isoxazoles in green media

Because of the wide ranging bioactivities associated with the benzimidazole nucleus, this review highlights the advances made in the synthesis of benzimidazole-based biheterocyclic molecules by combinatorial approaches.

Journal	Data powered by TypesetResearch on Chemical Intermediates
Publisher	Data powered by TypesetSpringer Science and Business Media LLC
ISSN	0922-6168
Open Access	0