Indazole: a medicinally important heterocyclic moiety

Thangadurai, Ananda; Minu, Maninder; Wakode, Sharad; Agrawal, S. S.; Narasimhan, Balasubramanian

doi:10.1007/s00044-011-9631-3

Cited by 135 publications

(60 citation statements)

References 50 publications

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“…23) We anticipated that benzophenone tosylhydrazone 6a would undergo intramolecular C-H amination with the aid of a palladium catalyst to afford 3-substituted indazoles 7a. 24) Through the systematic screenings of a range of palladium sources, reoxidants, and solvents, we found that the desired cyclization did occur in dimethyl sulfoxide (DMSO) at 50°C in the presence of a catalytic amount of Pd(OAc) 2 along with Cu(OAc) 2 as a reoxidant.…”

Section: )mentioning

confidence: 99%

Synthesis of Heterocyclic Compounds through Palladium-Catalyzed C–H Cyclization Processes

Inamoto

2013

CHEMICAL & PHARMACEUTICAL BULLETIN

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Herein, we describe our development of synthetic methods for heterocyclic compounds based on the palladium-catalyzed carbon-hydrogen bond (C-H) functionalization/intramolecular carbon-heteroatom (nitrogen or sulfur) bond formation process. By this C-H cyclization method, we efficiently prepared various N-heterocycles, including indazoles, indoles, and 2-quinolinones, as well as S-heterocycles such as benzothiazoles and benzo[b]thiophenes. Yields are typically good to high and good functional-group tolerance is observed for each process, thereby indicating that the method provides a novel, highly applicable synthetic route to the abovementioned biologically important heterocyclic frameworks. As an application of this approach, an auto-tandem-type, one-pot process involving the oxidative Heck reaction and subsequent C-H cyclization using cinnamamides and arylboronic acids as starting materials in the presence of a palladium catalyst was also developed for the rapid construction of the 2-quinolinone nucleus.

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Section: )mentioning

confidence: 99%

Synthesis of Heterocyclic Compounds through Palladium-Catalyzed C–H Cyclization Processes

Inamoto

2013

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…1 The manipulation of substitution pattern is crucial for designing pharmaceutical molecules bearing indazoles. We are interested in the introduction of a pyridinyl alkyl group into indazoles because some pyridinyl alkyl indazoles have shown important biological properties.…”

Section: Introductionmentioning

confidence: 99%

Microwave-assisted synthesis of 2-pyridinylethyl indazoles

Zhang

Chen

et al. 2015

Tetrahedron Letters

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“…This ring system serves as a core component of important nitrogen containing heterocycles that display a broad range of biological properties, such as the inhibition of nitric oxide 1 and HIV protease, 2 anti-inflammatory, 3 antitumor, 4 and anti-cancer 5 activities, and serotonin 5-HT3 receptor antagonist behavior. This ring system serves as a core component of important nitrogen containing heterocycles that display a broad range of biological properties, such as the inhibition of nitric oxide 1 and HIV protease, 2 anti-inflammatory, 3 antitumor, 4 and anti-cancer 5 activities, and serotonin 5-HT3 receptor antagonist behavior.…”

Section: Introductionmentioning

confidence: 99%