OMS-2 nanorod-supported cobalt catalyst for aerobic dehydrocyclization of vicinal diols and amidines: Access to functionalized imidazolones

Xie, Feng; Chen, Xiuwen; Zhang, Xiangyu; Luo, Chujun; Lin, Shizhuo; Li, Bin; Li, Yibiao; Zhang, Min

doi:10.1016/j.jcat.2021.04.022

Cited by 11 publications

(6 citation statements)

References 52 publications

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“…It indicates that this reaction probably does not involve a radical process. According to the results observed and the related literature, 13,14,18 a possible reaction mechanism is proposed (Scheme 5). Firstly, the condensation of 2-(1-methyl-1H-indol-3-yl)cyclohexanone (1a)…”

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confidence: 79%

“…According to the results observed and the related literature, 13,14,18 a possible reaction mechanism is proposed (Scheme 5). Firstly, the condensation of 2-(1-methyl-1 H -indol-3-yl)cyclohexanone ( 1a ) and benzimidamide hydrochloride ( 2a ) gives intermediate B , which is oxidized into intermediate C with the aid of Cu( ii ).…”

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confidence: 80%

“…For example, in 2021, Zhang and co-workers developed an OMS-2 nanorod-supported cobalt catalyzed rearrangement reaction of vicinal diols and amidines to synthesize spiroimidazolones (Scheme 1c). 13 In 2015, our group reported a metal-free protocol for the synthesis of spiroimidazolones via a base-promoted rearrangement reaction of amidines and cyclic ketones. To our regret, no products were generated when 2-substituted cyclo-hexanones were employed as substrates (Scheme 1d).…”

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confidence: 99%

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Cu-Catalyzed synthesis of spiroimidazole derivatives via an indolyl mediated cyclization–rearrangement reaction

Chen

Wei

et al. 2022

Org. Chem. Front.

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confidence: 80%

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Cu-Catalyzed synthesis of spiroimidazole derivatives via an indolyl mediated cyclization–rearrangement reaction

Chen

Wei

et al. 2022

Org. Chem. Front.

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“…This protocol consists of an important platform for the conversion of abundant and sustainable alcoholic resources into functional N-heterocycles. Zhang and coworkers [40] reported a new cobalt catalyst supported by highly dispersed manganese oxide nanorods of octahedral molecular sieve (OMS-2). Using this catalyst, the authors successfully accomplished the aerobic dehydrocyclization of neighboring diols and amidines to access various imidazolone structures.…”

Section: Scheme 4 Synthesis Of Quinazolinones Via An Acceptorless Coupling Of O-aminobenzamidesmentioning

confidence: 99%

Advances in Green Catalysis for the Synthesis of Medicinally Relevant N-Heterocycles

et al. 2021

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N-heterocycles, both saturated and unsaturated, are ubiquitous biologically active molecules that are extremely appealing scaffolds in drug discovery programs. Although classical synthetic methods have been developed to access many relevant N-heterocyclic scaffolds, representing well-established and reliable routes, some do not meet the needs of sustainability. In this context, several advances have been made towards the sustainable synthesis of N-heterocycles. This review focuses on the most recent examples from the last five years of catalytic synthesis of several heterocyclic compounds of medicinal relevance. Thus, the synthesis of isoindoloquinazolines, quinazolines and azaindoles, among others, are covered. The synthetic methods selected include the use of homogeneous and heterogeneous catalysts and the use of alternative and sustainable methods such as, for example, metal-catalyzed acceptorless coupling and one-pot reactions. The green aspects of the individual synthetic approaches are highlighted, and the scope of each methodology is described.

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“…As a part of our continuous efforts toward the construction of N-heterocycles using highly efficient nanocatalysts, 13 we recently reported the octahedral molecular sieve (OMS)-2 nanorods supported cobalt catalyzed aerobic dehydrocyclization reaction of vicinal diols and amidines (Scheme 2, eq a). 14 The substrate generality was examined by performing a coupling reaction between 3-aminopropane-1,2-diol 1a and benzamidine hydrochloride 2a. Surprisingly, the desired product 3aa′ was not formed, while an unexpected cyclized compound 3aa was obtained in 52% yield (Scheme 2, eq b).…”

Section: ■ Introductionmentioning

confidence: 99%

Layered Double Hydroxides as Reusable Catalysts for Cyclocondensation of Amidines and Aminoalcohols: Access to Multi-functionalized Oxazolines

et al. 2021

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An efficient catalytic protocol based on reusable MgAl-layered double hydroxides has been developed for the synthesis of multi-functionalized oxazolines via the cyclocondensation of amidines and aminoalcohols. The developed method has a broad substrate scope and excellent functional group tolerance and uses a reusable catalyst. The catalyst can be conveniently recycled by filtration and reused for at least five times without obvious deactivation. Additionally, the selective ortho C–H silylation of oxazolines was performed using Ru(II) as the catalyst and triethyl silane as the silylating reagent, which proved to be a convenient and practical method for the synthesis of versatile organosilyl-functionalized oxazolines with advantageous biological and physical properties.

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OMS-2 nanorod-supported cobalt catalyst for aerobic dehydrocyclization of vicinal diols and amidines: Access to functionalized imidazolones

Cited by 11 publications

References 52 publications

Cu-Catalyzed synthesis of spiroimidazole derivatives via an indolyl mediated cyclization–rearrangement reaction

Cu-Catalyzed synthesis of spiroimidazole derivatives via an indolyl mediated cyclization–rearrangement reaction

Advances in Green Catalysis for the Synthesis of Medicinally Relevant N-Heterocycles

Layered Double Hydroxides as Reusable Catalysts for Cyclocondensation of Amidines and Aminoalcohols: Access to Multi-functionalized Oxazolines

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