Article
Chemistry, Organic
Giang Le-Nhat-Thuy, Tuyet Anh Dang Thi, Phuong Hoang Thi, Quynh Giang Nguyen Thi, Ha-Thanh Nguyen, Doan Vu Ngoc, Tuan-Anh Nguyen, Tuyen Van Nguyen
Summary: An efficient method for preparing a series of novel 3-benzoyl-4H-benzo[g]chromene-5,10-dione derivatives from 2-hydroxy-1,4-naphthoquinone, aromatic aldehydes, and arylenaminones in glacial acetic acid under microwave irradiation was developed. The transformation involves a sequence of reactions including Knoevenagel condensation, dehydration, Michael addition, O-cyclization, proton transfer, elimination, deprotonation, and double bond isomerization.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Organic
Masashi Yokoya, Ryo Fujimoto, Tomoki Kato, Taku Hashimoto, Shinya Kimura, Naoki Saito, Masamichi Yamanaka
Summary: A facile photochemical strategy utilizing the photoredox reaction of quinones for C-H bond oxidation was developed to synthesize benzo[g]chromene derivatives. The intramolecular cyclization reaction proceeded via the formation of 1,3-dioxole compounds as intermediates. The synthesized derivatives possess important heterocyclic skeletons with useful biological and pharmacological properties.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Thuy Quynh Le, Chang Ho Oh
Summary: An efficient and facile method utilizing PTSA catalyst has been developed for the synthesis of 2,3-dihydronaphtho[2,3-b]furan and 3,4-dihydro-2H-benzo[g]chromene. This methodology shows high yield cyclization reaction of ortho-oxalate-, ortho-keto-, and ortho-formyl arylacetylenols. It is also successfully applied to the large-scale synthesis of the naphthofuran skeleton.
SYNTHETIC COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Masashi Yokoya, Takaaki Ishiguro, Yoshiaki Sakairi, Shinya Kimura, Yuji Morita, Masamichi Yamanaka
Summary: A novel and efficient method for synthesizing benzo[de]chromene-7,8-dione derivatives without post-oxidation of benzo[de]chromenes was developed. The synthesized compounds exhibited strong antimicrobial activity, particularly against multidrug efflux pump-deficient strains.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Ibrahim S. Al Nasr, Jana Jentzsch, Amin Shaikh, Priti Singh Shuveksh, Waleed S. Koko, Tariq A. Khan, Khursheed Ahmed, Rainer Schobert, Klaus Ersfeld, Bernhard Biersack
Summary: New pyranonaphthoquinone derivatives show varied activities against different parasites, indicating potential therapeutic value. Some derivatives exhibit antioxidant activities, suggesting potential for other biological activities.
CHEMISTRY & BIODIVERSITY
(2021)
Article
Chemistry, Multidisciplinary
Kevin Renault, Yoan Capello, Shun Yao, Sami Halila, Anthony Romieu
Summary: Latent cyclic carbon-centered nucleophiles, known as latent C-nucleophiles, have proven to be valuable in the field of reaction-based fluorescent probes. They are used to introduce a Michael acceptor moiety for analyte detection or to promote fluorogenic cascade reactions. C-nucleophiles with additional reactive handles offer opportunities for tuning properties and using ad hoc chemical moiety for drug-releasing capabilities. By exploring functionalized derivatives of barbituric acid, piperidine-2,4-dione, and Meldrum's acid, a versatile candidate suitable for structural optimization was identified. This study opens up possibilities for multifunctional fluorescence imaging probes and optically modulated theranostics.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Ravikumar Akunuri, Manasa Vadakattu, Grace Kaul, Abdul Akhir, Deepanshi Saxena, Mohammad Naiyaz Ahmad, Sushmitha Bujji, Swanand Vinayak Joshi, Arunava Dasgupta, Venkata Madhavi Yaddanapudi, Sidharth Chopra, Srinivas Nanduri
Summary: The synthesized 3,4-dihydro-1H-benzo[b]azepine-2,5-dione derivatives showed promising antibacterial properties against Staphylococcus aureus and Mycobacterium tuberculosis, making them potential candidates for further development.
Article
Chemistry, Multidisciplinary
Yunhe He, Hongxue Wang, Tingyu Gao, Jia Liu, Wenting Jiang, Hong Zhang
Summary: A new series of benzo[h]quinoline-based alpha-arylidene cycloketone derivatives, 9-arylidene-9,11-dihydro-8H-benzo[h]pyrano[3,4-b]quinolin-8-ones, were successfully synthesized in good yields through a Claisen-Schmidt condensation reaction of readily synthesized benzo[h]pyrano[3,4-b]quinolin-8-one with aromatic aldehydes under eco-friendly solvent-free conditions. The synthetic strategy is characterized by its experimental simplicity, affordable reagents, and satisfactory yields, making it a useful method.
RESEARCH ON CHEMICAL INTERMEDIATES
(2021)
Article
Chemistry, Organic
Toktam Shiebani Daloee, Farahnaz K. Behbahani
Summary: This study describes an easy access to highly functionalized 2-amino-5,10-dioxo-4-aryl-5,10-dihydro-4H-benzo[g]chromene-3-carbonitriles using a green procedure. The reaction of aldehydes, 2-hydroxy-1,4-naphthoquinone, and malononitrile in the presence of L-proline as an organocatalyst under reflux condition in ethanol was investigated. The study also reported the synthesis of some unprecedented compounds, and their chemical properties were evaluated using H-1 NMR technique.
POLYCYCLIC AROMATIC COMPOUNDS
(2022)
Article
Chemistry, Organic
Mahdieh Yahyazadehfar, Sayed Ali Ahmadi, Enayatollah Sheikhhosseini, Dadkhoda Ghazanfari
Summary: The paper presents a green, efficient method for the Knoevenagel condensation reaction using water as the solvent, bentonite as the catalyst, and elimination of the need for column purification of products.
LETTERS IN ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Diksha Rajput, Dolma Tsering, Muthu Karuppasamy, Kamal K. Kapoor, Subbiah Nagarajan, C. Uma Maheswari, Nattamai Bhuvanesh, Vellaisamy Sridharan
Summary: An efficient synthetic method for oxazepino[5,4-b]quinazolin-9-ones, 6H-chromeno[4,3-b]quinolines, and dibenzo[b,h][1,6]naphthyridines was established using a substrate-based approach under microwave-assisted and conventional heating conditions, achieving high yields (up to 88%). The one-pot process involved CuBr2-catalyzed cascade annulation and delivered oxazepino[5,4-b]quinazolin-9-ones with two new heterocyclic rings and three new C-N bonds. Microwave assistance was found to be superior, providing clean and rapid reactions completed in 15 minutes, compared to longer reaction times and elevated temperatures required for conventional heating.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Biochemical Research Methods
Debora Batista Pinheiro-Sousa, Mayara Ingrid Sousa Lima, Ricardo Mendes Goncalves, Debora Martins Silva Santos, Alcina Vieira de Carvalho Neta, Laercio dos Anjos Benjamim, Gilvanda Silva Nunes, Paulo Roberto Brasil de Oliveira Marques, Raimunda Nonata Fortes Carvalho-Neta
Summary: In this study, the in situ interaction between BZA and ct-dsDNA was evaluated using an electroanalytical genosensor. The interaction showed processes of intercalation, degradation, and breaks of the double strand of ct-dsDNA, indicating high toxicity. The genosensor demonstrated good reproducibility and stability, providing a quick alternative for assessing the toxicity of toxic xenobiotics and biologically electroactive molecules like DNA.
ANALYTICAL BIOCHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Ashiq Hussain Padder, Mohammad Yaqoob Bhat, H. Surya Prakash Rao, Raman Gupta, Qazi Naveed Ahmed
Summary: A new synthesis of 4,5-dihydro-1H-benzo[g]indazole derivatives from novel enaminones via Blaise reaction is reported. The protocol is simple, rapid, and efficient, and does not require a catalyst, organic co-solvent, or additive. Polyethylene glycol (PEG-400) is used as a recyclable medium, and microwave irradiation is employed to achieve yields of 91-95% without the need for chromatography.
Article
Chemistry, Organic
Bikoshita Porashar, Subhamoy Biswas, Archana Kumari Sahu, Archana Chutia, Anil K. Saikia
Summary: In this study, tetrahydro-4H-pyrrolo[3,2-c]quinolin-4-ones and dihydro-1H-benzo[b]azepines were efficiently synthesized from 2-aminobenzonitriles and donor-acceptor cyclopropanes using SnCl4 as a catalyst. The reaction involves cyclopropane ring opening and nucleophilic attack by amine, followed by unprecedented rearrangement at two different reaction temperatures, resulting in the formation of two nitrogen heterocycles. This methodology can be used for the synthesis of hexahydropyrrolo[3,2-c]quinolinone derivatives, which are present in biologically active molecules.
Article
Chemistry, Organic
Boris V. V. Lichitsky, Andrey N. N. Komogortsev, Valeriya G. G. Melekhina
Summary: An efficient method for the telescoped synthesis of a novel polycyclic compound was developed using a one-pot multicomponent reaction. The advantages of this method include the use of readily available starting reagents, high atom economy, and a simple procedure for preparation and purification of the target product.
