Solid-Phase Synthesis of 1,3,4-Oxadiazole and 1,3,4-Thiadiazole Derivatives via Selective, Reagent-Based Cyclization of Acyldithiocarbazate Resins

The chemistry of heterocyclic compounds has been an interesting field of study for a long time. Heterocyclic nucleus 1,3,4-thiadiazole constitutes an important class of compounds for new drug development. The synthesis of novel thiadiazole derivatives and investigation of their chemical and biological behavior have gained more importance in recent decades. The search for antiepileptic compounds with more selective activity and lower toxicity continues to be an active area of intensive investigation in medicinal chemistry. During the recent years, there has been intense investigation of different classes of thiadiazole compounds, many of which possess extensive pharmacological activities, namely, antimicrobial activity, anticonvulsant, antifungal antidiabetic, anti-inflammatory, antioxidant, and antituberculosis activities, and so forth. The resistance towards available drugs is rapidly becoming a major worldwide problem. The need to design new compounds to deal with this resistance has become one of the most important areas of research today. Thiadiazole is a versatile moiety that exhibits a wide variety of biological activities. Thiadiazole moiety acts as “hydrogen binding domain” and “two-electron donor system.” It also acts as a constrained pharmacophore. On the basis of the reported literature, we study here thiadiazole compounds and their synthetic methods chemistry and anticonvulsant activity.

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“…(e) From Resin . Resin with TMSCl, MCPBA, and R 2 R 3 NH gave 1,3,4-S thiadiazole [ 16 ] ( Scheme 10 ).…”

Section: Synthetic Procedures Of 134-thiadiazolesmentioning

confidence: 99%

Synthetic Methods, Chemistry, and the Anticonvulsant Activity of Thiadiazoles

Sharma

Verma

Prajapati

et al. 2013

International Journal of Medicinal Chemistry

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“…Recently, a solid-phase synthetic route using the Merrifield resin (611) has been utilized to prepare various substituted-1,3,4-thiadiazoles 613, by a dehydrative cyclization of acyldithiocarbazate resins 612 with TMSCl in DCE at 60 C [306]. Acyldithiocarbazate resins 612 have been prepared by reaction of the Merrifield resin 611 with carbon disulfide, various hydrazides, and NaH (Scheme 14.168).…”

Section: Thermodynamic Aspectsmentioning

confidence: 99%

“…A solid-phase synthetic route, from Merrifield resin, has been exploited to prepare various 2-amino-5-substituted-1,3,4-thiadiazoles (849) by nucleophilic displacement of the sulfonyl group (Scheme 14.241) [306].…”

Section: Reactivitymentioning

confidence: 99%

Thiadiazoles

Chiacchio

Romeo

2011

Modern Heterocyclic Chemistry

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“…The thiocarbamoyl structure of dithiocarbazate shows various biological activities like antibacterial, antifungal, anti-inflammatory and uncoupling activity [6]. Their extensive use in pharmaceuticals [7][8][9], agrochemicals [10], organic synthesis [11][12][13], coordination chemistry [14][15][16] peptide synthesis [17], solid phase organic synthesis [18] and complexation reactions with transition metals [19,20] make them a unique hetero compound. The donor ligand complexation reaction of dithiocarbazate with transition metal is of considerable interest due to high biological activity [21,22].…”

Section: Introductionmentioning

confidence: 99%

Triton-B Catalyzed, Green and Efficient Method for the Synthesis of Dithiocarbazates

Zaidi¹,

Saxena²

2019

Asian J. Chem.

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A novel, solvent free and high yielding method was accomplished for one-pot synthesis of dithiocarbazates by the reaction of various alkyl halides (primary, secondary and tertiary) with variety of substituted hydrazines using Triton-B (benzyl-trimethylammonium hydroxide) and carbon di sulphide. This new method of synthesizing dithiocarbazates involves mild conditions, simple procedures and high yields of the products as compared to previously used methods.

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Solid-Phase Synthesis of 1,3,4-Oxadiazole and 1,3,4-Thiadiazole Derivatives via Selective, Reagent-Based Cyclization of Acyldithiocarbazate Resins

Cited by 72 publications

References 35 publications

Synthetic Methods, Chemistry, and the Anticonvulsant Activity of Thiadiazoles

Synthetic Methods, Chemistry, and the Anticonvulsant Activity of Thiadiazoles

Thiadiazoles

Triton-B Catalyzed, Green and Efficient Method for the Synthesis of Dithiocarbazates

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