C–H Bond Alkenylation

Satoh, Tetsuya; Miura, Masahiro

doi:10.1002/9783527655588.ch18

Cited by 5 publications

(2 citation statements)

References 125 publications

(75 reference statements)

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“…In addition to the above medical applications, benzimidazole derivatives have been widely used as an essential part of biological applications including: antihypertensive activity, 154 155 156 157 158 antiprotozoal activity, 159–163 antiviral activity, 164–167 anthelmintic activity, 168 169 170 171 172 antidiabetic agents, 173 174 175 176 177 analgesic activity, 78 , 178 179 180 181 antispasmodic activity, 182 183 antidepressant activity, 184 185 186 187 188 189 sphingosine kinase 1 inhibitor, 190 191 anti-Alzheimer’s agents, 192 193 194 angiotensin II-AT1 receptor antagonists, 195 196 197 198 199 200 antiulcer activity, 201 202 203 204 anti-tubercular activity, 205 206 207 208 209 210 211 anti-HIV agents, 212 213 214 215 216 217 218 and anti-secretory activity. 219 220 221…”

Section: Biological Activity Of Benzimidazole Derivativesmentioning

confidence: 99%

A Review on Benzimidazole Heterocyclic Compounds: Synthesis and Their Medicinal Activity Applications

Alheety,

Mohammed,

Farhan

et al. 2023

SynOpen

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Benzimidazole is a heterocyclic compound formed by fusing the benzene ring with an imidazole ring that contains two nitrogen atoms. Benzimidazole and its derivatives are prepared in different ways, including condensation of o-phenylenediamine with carbonyl compounds (aldehydes and ketones) or with carboxylic acids and their derivatives. The benzimidazoles can also be prepared by rearranging other heterocyclic compounds such as quinoxaline derivatives, triazole derivatives, etc. In recent decades, benzimidazoles were prepared using green methods such as microwaves, ultrasound, and the use of an environmentally friendly catalyst, as well as photochemical reactions. Benzimidazoles have attracted the interest of scientists and researchers due to the great medical efficacy shown by them for various diseases. The benzimidazole derivatives show many pharmacological activities such as anticancer, anti-inflammatory, antioxidant, anticoagulant, antiviral, etc. This review focuses on shedding light on benzimidazole and its derivatives, the most important methods used to prepare it, as well as the biological applications in our daily lives.

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Section: Biological Activity Of Benzimidazole Derivativesmentioning

confidence: 99%

A Review on Benzimidazole Heterocyclic Compounds: Synthesis and Their Medicinal Activity Applications

Alheety,

Mohammed,

Farhan

et al. 2023

SynOpen

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“…In contrast to arylation and alkylation reactions, the installation of alkenyl groups onto the pyrazole ring has had limited success. − Consistent with low regioselectivity in the arylation of unsubstituted pyrazoles, an alkenylation reaction of 1-methylpyrazole gave a mixture of regioisomers (Figure A). , Furthermore, the Lewis basic nitrogen atom serves as a directing group for C–H functionalization at the neighboring arene ring, rather than the pyrazole ring (Figure B) . Lewis basicity was also attributed to the failure of pyrazole alkenylation using a directing group strategy that was successful in the regioselective C–H alkenylation of indoles .…”

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confidence: 99%

Direct C–H Alkenylation of Functionalized Pyrazoles

2015

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We have developed inter- and intramolecular C-H alkenylation reactions of pyrazoles. The catalyst, derived from Pd(OAc)2 and pyridine, enabled the oxidative alkenylation of pyrazoles containing a variety of functional groups at the C4 position. Activated alkenes, including acrylate, acrylamide, and styrene derivatives, and enamides could be installed in this process. The sequential C-H alkenylation and cyclization reactions gave rise to fused bicyclic pyrazoles, providing a new strategy to annulate readily available pyrazole compounds.

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Ligand‐controlled Regiodivergent C−H Alkenylation of Pyrazoles and its Application to the Synthesis of Indazoles

Kim

Kang

et al. 2017

Angewandte Chemie

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Regioselective C4‐, C5‐, and di‐alkenylations of pyrazoles were achieved. An electrophilic Pd catalyst generated by trifluoroacetic acid (TFA) and 4,5‐diazafluoren‐9‐one (DAF) leads to C4‐alkenylation, whereas KOAc and mono‐protected amino acid (MPAA) ligand Ac‐Val‐OH give C5‐alkenylation. A combination of palladium acetate, silver carbonate, and pivalic acid affords dialkenylation products. Annulation through sequential alkenylation, thermal 6π‐electrocyclization, and oxidation gives functionalized indazoles. This comprehensive strategy greatly expands the range of readily accessible pyrazole and indazole derivatives, enabling useful regiodivergent C−H functionalization of pyrazoles and other heteroaromatic systems.

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C–H Bond Alkenylation

Cited by 5 publications

References 125 publications

A Review on Benzimidazole Heterocyclic Compounds: Synthesis and Their Medicinal Activity Applications

A Review on Benzimidazole Heterocyclic Compounds: Synthesis and Their Medicinal Activity Applications

Direct C–H Alkenylation of Functionalized Pyrazoles

Ligand‐controlled Regiodivergent C−H Alkenylation of Pyrazoles and its Application to the Synthesis of Indazoles

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