The conversion of isothiazoles into pyrazoles using hydrazine

Ioannidou, H. A.; Koutentis, P. A.

doi:10.1016/j.tet.2009.06.041

Cited by 45 publications

(20 citation statements)

References 66 publications

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“…proximal to the S). 155 Although SMC reactions of parent 4,5-, 156 3,5- 157 or 3,4-dihaloisothiazoles 158 do not appear to have been reported, the additionally C -substituted derivatives in our data conform to a trend whereby reaction occurs at C5 ( i.e. proximal to the S) then at C3 ( i.e.…”

Section: Key Heteroarene Ring-systems On a Case-by-case Basiscontrasting

confidence: 60%

Site-selective Suzuki–Miyaura coupling of heteroaryl halides – understanding the trends for pharmaceutically important classes

et al. 2017

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Section: Key Heteroarene Ring-systems On a Case-by-case Basiscontrasting

confidence: 60%

Site-selective Suzuki–Miyaura coupling of heteroaryl halides – understanding the trends for pharmaceutically important classes

et al. 2017

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“…In 2009, Koutentis and co‐workers observed the hydrazine‐promoted rearrangement of isothiazoles to pyrazoles (Scheme ) . This interesting reaction is mechanistically related to heterocyclic ring rearrangement reactions with tethered nucleophilic groups, and requires an electron‐withdrawing substituent on the isothiazole ring to afford good results.…”

Section: Reactivity Of Isothiazolesmentioning

confidence: 99%

Recent Advances in the Synthesis and Reactivity of Isothiazoles

2019

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Isothiazoles represent an important class of five‐membered sulfur heterocycles that are widely utilized in medicinal chemistry and organic synthesis due to the unique properties of two electronegative heteroatoms in a 1,2‐relationship. However, in contrast to other 1,2‐azoles, the facile assembly of isothiazoles has always been considered a substantial challenge. In the last decade, major advances have taken place in the fields of synthesis and functionalization of isothiazoles that make them accessible to a wide range of interested chemists through unprecedented pathways. New condensation methods have emerged that address the challenges posed by unstable thiohydroxylamine. New metal‐catalyzed approaches have been reported that deliver densely decorated isothiazoles bearing various sensitive functional groups. New functionalization strategies have been developed through both cross‐coupling and direct C−H activation chemistry. Finally, the emergence of novel heterocyclic architectures based on isothiazole opens the door for future investigations of this versatile heterocyclic scaffold. This review covers the period from January 2004 to December 2018 and is intended as a sequel to the review on isoxazoles, which represent another class of synthetically‐important 1,2‐azoles (see Adv. Synth. Catal. 2015, 357, 2583–2614).

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“…With the model in hand, we screened an in-house library of 107 isothiazoles (36)(37)(38)(39) in the hope that new isothiazole targets could be identified. The model gave a wide range of predicted activities ()5.377 to )0.041); however, all predictions were outside the domain of applicability (134.188-22.445, threshold of 10.968).…”

Section: In Silico Exploration Of Mek Inhibitorsmentioning

confidence: 99%

“…Observed and Predicted values for the training and test set (compounds[33][34][35][36][37][38][39][40][41][42][43][44][45][46][47] …”

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In Silico Exploration for Identifying Structure–Activity Relationship of MEK Inhibition and Oral Bioavailability for Isothiazole Derivatives

et al. 2010

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In this study, quantitative structure-activity ⁄ property models are developed for modeling and predicting both MEK inhibitory activity and oral bioavailability of novel isothiazole-4-carboxamidines. The models developed are thoroughly discussed to identify the key components that influence the inhibitory activity and oral bioavailability of the selected compounds. These selected descriptors serve as a first guideline for the design of novel and potent MEK inhibitors with desired ADME properties.

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The conversion of isothiazoles into pyrazoles using hydrazine

Cited by 45 publications

References 66 publications

Site-selective Suzuki–Miyaura coupling of heteroaryl halides – understanding the trends for pharmaceutically important classes

Site-selective Suzuki–Miyaura coupling of heteroaryl halides – understanding the trends for pharmaceutically important classes

Recent Advances in the Synthesis and Reactivity of Isothiazoles

In Silico Exploration for Identifying Structure–Activity Relationship of MEK Inhibition and Oral Bioavailability for Isothiazole Derivatives

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