Synthesis of linear dibenzo[1,8]naphthyridines using 2-chloro-4-methylquinolines

Manickam, Manoj; Prasad, K. J. Rajendra

doi:10.3998/ark.5550190.0012.922

Cited by 5 publications

(2 citation statements)

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“…π-Extended 1,4- and 1,3 a -diheteraphenalenes, represented mostly by quinolino[4,3,2- kl ]acridines and phenoxazine derivatives, respectively, are discussed at the end of this section. For reported examples of 1,3- and 1,9-diheteraphenalenoid systems, see refs − .…”

Section: Phenalenoidsmentioning

confidence: 99%

Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

et al. 2016

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Two-dimensionally extended, polycyclic heteroaromatic molecules (heterocyclic nanographenes) are a highly versatile class of organic materials, applicable as functional chromophores and organic semiconductors. In this Review, we discuss the rich chemistry of large heteroaromatics, focusing on their synthesis, electronic properties, and applications in materials science. This Review summarizes the historical development and current state of the art in this rapidly expanding field of research, which has become one of the key exploration areas of modern heterocyclic chemistry.

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Section: Phenalenoidsmentioning

confidence: 99%

Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

et al. 2016

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“…Due to their biological and synthetic importance, the development of effective routes to synthesize naphthyridines continues to be an active area of research for synthetic organic chemists [11]. A survey of the literature shows that the major synthetic approaches used to prepare the naphthyridine system involved condensation of 2-aminopyridine derivatives with carbonyl compounds containing an activated methylene group [12,13,14,15,16,17,18,19] or with β -ketoesters [20].…”

Section: Introductionmentioning

confidence: 99%

Microwave-Assisted Synthesis of Novel Pyrazolo[3,4-g][1,8]naphthyridin-5-amine with Potential Antifungal and Antitumor Activity

et al. 2015

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Abstract:The microwave assisted reaction between heterocyclic o-aminonitriles 1 and cyclic ketones 2 catalyzed by zinc chloride led to new series of pyrazolo [3,4-b] [1,8]naphthyridin-5-amines 3 in good yields. This procedure provides several advantages such as being environmentally friendly, high yields, simple work-up procedure, broad scope of applicability and the protocol provides an alternative for the synthesis of pyrazolonaphthyridines. The whole series showed antifungal activities against Candida albicans and Cryptococcus neoformans standardized strains, being compounds with a 4-p-tolyl substituent of the naphthyridin scheleton (3a, 3d and 3g), the most active ones mainly against C. albicans, which appear to be related to their comparative hydrophobicity. Among them, 3d, containing a cyclohexyl fused ring, showed the best activity. The anti-Candida activity was corroborated by testing the three most active compounds against clinical isolates of albicans and non-albicans Candida strains. These compounds were also screened by the US National Cancer Institute (NCI) for their ability to inhibit 60 different human tumor cell lines. Compounds 3a and 3e showed remarkable OPEN ACCESSMolecules 2015, 20 8500 antitumor activity against cancer cell lines, with the most important GI50 values ranging from 0.62 to 2.18 μM.

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Efficient Synthesis of Functionalized Benzo[b][1,8]naphthyridine Derivatives via Three-Component Reaction Catalyzed by l-Proline

Lin

et al. 2014

ACS Comb. Sci.

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Synthesis of linear dibenzo[1,8]naphthyridines using 2-chloro-4-methylquinolines

Abstract: The attempted synthesis of linear dibenzonaphthyridines utilizing 2-chloro-4-methylquinolines leads to the formation of hitherto unknown compounds. The reaction of 2-chloro-4-methylquinoline with 2-amino-5-chlorobenzophenone afforded 6-chloro-10H-dibenzo [b,g]

Cited by 5 publications

References 20 publications

Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

Microwave-Assisted Synthesis of Novel Pyrazolo[3,4-g][1,8]naphthyridin-5-amine with Potential Antifungal and Antitumor Activity

Efficient Synthesis of Functionalized Benzo[b][1,8]naphthyridine Derivatives via Three-Component Reaction Catalyzed by l-Proline

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