Construction of Nitrogen‐Containing Heterocycles by CH Bond Functionalization

Thansandote, Praew; Lautens, Mark

doi:10.1002/chem.200900281

Cited by 523 publications

(129 citation statements)

References 126 publications

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“…The reaction fails to occur, or gives poor yields of (4aa) using hydroxides ( 3 /P(t-Bu) 3 (Table 3, entry 7). Low yields were obtained with P(n-Bu) 3 (Table 3, entry 6), this may be due to the bulky or oppy nature of the phosphane butyl chains causing signicant stereo-hindrance within the coordination sphere of the metal. The presence of the i-Pr groups in Ruphos might explain the lower yields (Table 3, entry 4) compared with those for Sphos (Table 3, entry 3) and CyJohnPhos (Table 3 entry 2).…”

Section: Resultsmentioning

confidence: 99%

A catalytic route to dibenzodiazepines involving Buchwald–Hartwig coupling: reaction scope and mechanistic consideration

et al. 2015

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We report a new synthetic method for the synthesis of a family of dibenzodiazepines (DBDAs), employing Pd-catalyzed C-N coupling of o-bromoaldimine, with o-bromoaniline as the key step. Eleven DBDAs were prepared, containing electron-withdrawing groups (CN, F, NO 2 ) and electron-donating groups (OMe). The reaction conditions were optimized (catalyst, phosphine, base and solvent) and best results were obtained with Pd(OAc) 2 , SPhos, Cs 2 CO 3 in THF. Due to the ambiguity of the mechanism at hand, various mechanistic studies were performed, that included DFT calculations. The oxidative addition process was studied in detail by DFT, and these studies supported the observed reaction regioselectivity. The adducts formed between the aldimine and the Pd(0) catalyst were calculated to be more stable than the ones formed with the amine, and the barrier for the oxidative addition at the C-Br bond of the aldimine was calculated to be lower than the one at the C-Br bond of the aryl amine. The formation of DBDA over the dibenzoaminopiperidine has been explained in the final cyclization step.

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Section: Resultsmentioning

confidence: 99%

A catalytic route to dibenzodiazepines involving Buchwald–Hartwig coupling: reaction scope and mechanistic consideration

et al. 2015

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“…The biological activity manifested by tricyclic, nitrogencontaining heterocyclic compounds, makes them attractive targets for synthetic chemists [1][2][3]. The seven-membered ring 5H-dibenz[b,f]azepine nucleus (1) is a pharmaceutically important structure and constitutes the key subunit in tricyclic antidepressant drug substances such as carbamazepine (1a) and oxcarbazepine (1b) (Figure 1) [4].…”

Section: Introductionmentioning

confidence: 99%

5H-Dibenz[b,f]azepine based pyrazole sulphonamides: A privileged platform for probing the antimicrobial and antioxidative properties

Kumar

Rangaswamy³

et al. 2015

Eur. J. Chem.

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“…12) Our group has been working on the palladium-catalyzed formation of C-N and C-S bonds via C-H functionalization, specifically applying it to intramolecular processes, which would provide novel routes to N-and Sheterocycles. 7,13,14) The working hypothesis at our starting point is shown in Chart 1. The treatment of compound 1, which possesses a heteroatom-based nucleophilic part (YH, Y= NR or S, which also functions as a directing group), with a palladium(II) catalyst forms palladium complex 3 via 2.…”

Section: Introductionmentioning

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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Construction of Nitrogen‐Containing Heterocycles by CH Bond Functionalization

Cited by 523 publications

References 126 publications

A catalytic route to dibenzodiazepines involving Buchwald–Hartwig coupling: reaction scope and mechanistic consideration

A catalytic route to dibenzodiazepines involving Buchwald–Hartwig coupling: reaction scope and mechanistic consideration

5H-Dibenz[b,f]azepine based pyrazole sulphonamides: A privileged platform for probing the antimicrobial and antioxidative properties

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

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