Diisopropylcarbodiimide: A Novel Reagent for the Synthesis of 1,3,4-Oxadiazoles on Solid-Phase

doi:10.1055/s-2000-6454

Cited by 7 publications

(2 citation statements)

References 4 publications

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“…Because the reactions were accomplished mainly under basic conditions, the acid-labile linkers were preferable. One of the first reports was presented by Brown et al, who reported on the solid-phase synthesis of 2,5-disubstituted 1,3,4-oxadiazoles from resin-bound 1,2-diacylhydrazines 1,3-diisopropyl carbodiimide (DIC) as a dehydrative agent . Acid-sensitive Rink resin was used as a solid support.…”

Section: Introductionmentioning

confidence: 99%

Current Parallel Solid-Phase Synthesis of Drug-like Oxadiazole and Thiadiazole Derivatives for Combinatorial Chemistry

Abdildinova

Gong

2018

ACS Comb. Sci.

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Solid-phase organic synthesis is a powerful tool in the synthesis of small organic molecules and building of libraries of compounds for drug discovery. Heterocyclic compounds are important components of the drug discovery field as well and serve as a core for hundreds of marketed drugs. In particular, oxadiazole and thiadiazole cores are compounds of great interest due to their comprehensive biological activities and structural features. Therefore, a plethora of oxadiazole and thiadiazole synthesis methodologies have been reported to date, including solution and solid-phase synthesis methodologies. In this review, we concentrate on and summarize solid-phase synthetic approaches of the oxadiazole and thiadiazole derivatives.

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Section: Introductionmentioning

confidence: 99%

Current Parallel Solid-Phase Synthesis of Drug-like Oxadiazole and Thiadiazole Derivatives for Combinatorial Chemistry

Abdildinova

Gong

2018

ACS Comb. Sci.

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“…Brill reported 1,3,4-oxadiazole synthesis as a traceless release on the solid support and Lee reported synthesis of 2-amido-1,3,4-oxadiazole derivatives on solid-phase synthesis. Clemens used diisopropylcarbodiimide to afford 1,3,4-oxadiazole from semicarbazide intermediate on solid-phase synthesis . Synthesis of 1,3,4-thiadiazoles on solid-phase was reported by Liu .…”

Section: Introductionmentioning

confidence: 99%

A Highly Efficient Diversification of 2-Amino/Amido-1,3,4-oxadiazole and 1,3,4-Thiadiazole Derivatives via Reagent-Based Cyclization of Thiosemicarbazide Intermediate on Solid-Phase

et al. 2015

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A 2-amino/amido-1,3,4-oxadiazole and 1,3,4-thiadiazole library has been constructed on solid-phase organic synthesis. The key step on this solid-phase synthesis involves the preparation of polymer-bound 2-amino-1,3,4-oxadiazole and 1,3,4-thiadiazole core skeleton resin by cyclization of thiosemicarbazide with EDC·HCl and p-TsCl, respectively. The resulting core skeleton undergoes functionalization reaction with various electrophiles such as alkyl halides, and acid chlorides to generate N-alkylamino and N-acylamino-1,3,4-oxadiazole, and 1,3,4-thiadiazole resin, respectively. Finally, the 2-amino and 2-amido-1,3,4-oxadiazole and 1,3,4-thiadiazole library was then generated in good yields and high purities by cleavage of the respective resin under trifluoroacetic acid(TFA) in dichloromethane(DCM). The constructed library shows reasonable, oral bioavailability drug properties as determine by using the Lipinski's Rule and similar parameters.

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Synthesis of Heterocycles Using Polymer-Supported Reagents under Microwave Irradiation

Crosignani¹,

Linclau

2006

Topics in Heterocyclic Chemistry

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Diisopropylcarbodiimide: A Novel Reagent for the Synthesis of 1,3,4-Oxadiazoles on Solid-Phase

Abstract: Using diisopropylcarbodiimide (DIPCDI) in DMF to effect cyclodehydration, various resin bound 1,2-diacylhydrazines were converted to the corresponding 2,5-disubstituted 1,3,4-oxadiazoles in good yields and purities.

Cited by 7 publications

References 4 publications

Current Parallel Solid-Phase Synthesis of Drug-like Oxadiazole and Thiadiazole Derivatives for Combinatorial Chemistry

Current Parallel Solid-Phase Synthesis of Drug-like Oxadiazole and Thiadiazole Derivatives for Combinatorial Chemistry

A Highly Efficient Diversification of 2-Amino/Amido-1,3,4-oxadiazole and 1,3,4-Thiadiazole Derivatives via Reagent-Based Cyclization of Thiosemicarbazide Intermediate on Solid-Phase

Synthesis of Heterocycles Using Polymer-Supported Reagents under Microwave Irradiation

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