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1.
Dr. Christopher R. Opie Dr. Hidetoshi Noda Prof. Dr. Masakatsu Shibasaki Dr. Naoya Kumagai 《Chemistry (Weinheim an der Bergstrasse, Germany)》2019,25(18):4648-4653
The B3NO2 six-membered heterocycle (1,3-dioxa-5-aza-2,4,6-triborinane=DATB), comprising three different non-carbon period 2 elements, has been recently demonstrated to be a powerful catalyst for dehydrative condensation of carboxylic acids and amines. The tedious synthesis of DATB, however, has significantly diminished its utility as a catalyst, and thus the inherent chemical properties of the ring system have remained virtually unexplored. Here, a general and facile synthetic strategy that harnesses a pyrimidine-containing scaffold for the reliable installation of boron atoms is disclosed, giving rise to a series of Pym-DATBs from inexpensive materials in a modular fashion. The identification of a soluble Pym-DATB derivative allowed for the investigation of the dynamic nature of the B3NO2 ring system, revealing differential ring-closing and -opening behaviors depending on the medium. Readily accessible Pym-DATBs proved their utility as efficient catalysts for dehydrative amidation with broad substrate scope and functional-group tolerance, offering a general and practical catalytic alternative to reagent-driven amidation. 相似文献
2.
I. V. Ukrainets L. V. Sidorenko O. V. Gorokhova N. A. Jaradat 《Chemistry of Heterocyclic Compounds》2006,42(4):475-487
Various methods of synthesizing amides of 2-hydroxy-4-imino-1,4-dihydroquinoline-3-carboxylic acids have been studied. Results
of investigations on the antitubercular and antiinflammatory activity of the obtained compounds are discussed.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 542–555, April, 2006. 相似文献
3.
I. V. Ukrainets L. V. Sidorenko O. V. Gorokhova S. V. Shishkina 《Chemistry of Heterocyclic Compounds》2006,42(6):776-781
Alkaline hydrolysis of the ethyl ester of 4-(cyanoethoxycarbonylmethyl)-2-oxo-1,2-dihydroquinoline-3-carboxylic acid is accompanied
by decarboxylation with loss of two molecules of CO2 and leads to 4-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 887–893, June, 2006. 相似文献
4.
I. V. Ukrainets E. V. Mospanova L. V. Sidorenko 《Chemistry of Heterocyclic Compounds》2007,43(7):863-870
An improved method is reported for the synthesis of a series of 1-hydroxy-3-oxo-5,6-dihydro-3H-pyrrolo[3,2,1-ij]quinoline-2-carboxylic
acid hetarylamides. The antitubercular activity of all of the compounds prepared has been studied. The structure-biological
activity dependence revealed is discussed.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 1023–1033, July, 2007. 相似文献
5.
Kazunori WakasugiAtsushi Nakamura Akira IidaYoshinori Nishii Nobuji NakataniShoji Fukushima Yoo Tanabe 《Tetrahedron》2003,59(28):5337-5345
Various carboxylic esters or amides were prepared in good to excellent yield between carboxylic acids and equimolar amounts of alcohols or amines under very mild conditions (0-45°C; within 3 h) using dimethylsulfamoyl chloride (Me2NSO2Cl; 1) combined with N,N-dimethylamines (Me2NR: 2a; R=Me, 2b; R=Bu). The choice of the sulfamoyl chloride and the amine is crucial for the reaction; that is, sterically uncrowded amines accelerated the present esterification and amidation. This agent had some advantages over methanesulfonyl chloride (3)/amines as for the atom-economy, avoidance of side reactions, and had very high chemoselectivity toward the carboxyl group vs the hydroxyl group; the experiment was performed by the addition of 1 to the mixture of carboxylic acids and alcohols. Application of this method to the synthesis of coumaperine, a chemopreventive natural product, was performed using the present amidation as a key step. 相似文献
6.
Ravil I. Khusnutdinov Tatyana M. Egorova Rishat I. Aminov Yulia Yu. Mayakova Ekaterina S. Mescheryakova 《合成通讯》2020,50(4):564-570
AbstractFeCl3·6H2O-catalyzed Ritter amidation of deltacyclene and hexacyclic norbornadiene dimers containing both a double bond and a three-carbon ring in the molecule with acetonitrile and water was performed. Depending on the hydrocarbon structure, the reaction proceeds via C-C bond cleavage in the three-carbon ring or at the double bond to form the corresponding N-acetamides. 相似文献
7.
Gundurao Kolavi 《Tetrahedron letters》2006,47(16):2811-2814
Novel heterocyclic systems 2-alkyl/aryl-9-(2-hydroxybenzylidene)-7,9-dihydro-8H-[1,3,4]thiadiazolo[2′,3′:2,3]imidazo[4,5-d][1,2]diazepin-8-one and 9-(2-hydroxy-benzylidene)-3,3-dimethyl-3,4,7,9-tetrahydro-2H-11-thia-4b,6,7,10-tetraazaindeno[1,2-a]azulene-1,8-dione are synthesized via an intramolecular amidation reaction. An interesting ring opening and cyclization of 2-alkyl/aryl-6-(2-oxo-2H-chromen-3-yl)imidazo[2,1-b][1,3,4]thiadiazole-5-carbaldehyde and 6,6-dimethyl-8-oxo-2-(2-oxo-2H-chromen-3-yl)-5,6,7,8-tetrahydroimidazo[2,1-b][1,3]benzothiazole-3-carbaldehyde are discussed. 相似文献
8.
Sarosh Iqbal Nimra Naveed Shaikh Khalid Mohammed Khan Shumaila Kiran Sehrish Naz Zaheer Ul-Haq Shahnaz Perveen M. Iqbal Choudhary 《Molecules (Basel, Switzerland)》2022,27(22)
Currently the discovery and development of potent β-glucuronidase inhibitors is an active area of research due to the observation that increased activity of this enzyme is associated with many pathological conditions, such as colon cancer, renal diseases, and infections of the urinary tract. In this study, twenty-seven 2-aminopyrimidine derivatives 1–27 were synthesized by fusion of 2-amino-4,6-dichloropyrimidine with a variety of amines in the presence of triethylamine without using any solvent and catalyst, in good to excellent yields. All synthesized compounds were characterized by EI-MS, HREI-MS and NMR spectroscopy. Compounds 1–27 were then evaluated for their β-glucuronidase inhibitory activity, and among them, compound 24 (IC50 = 2.8 ± 0.10 µM) showed an activity much superior to standard D-saccharic acid 1,4-lactone (IC50 = 45.75 ± 2.16 µM). To predict the binding mode of the substrate and β-glucuronidase, in silico study was performed. Conclusively, this study has identified a potent β-glucuronidase inhibitor that deserves to be further studied for the development of pharmaceutical products. 相似文献
9.
Mohamed Ould M’hamed 《合成通讯》2013,43(22):2511-2528
This review aims to present the application of ball milling for the synthesis ofdifferent heterocyclic compounds in very good yields. The method is a simple, economical, and ecofriendly process for synthesizing heterocycles, which is a large family of organic compounds. They are extremely important and have wide-ranging pharmaceutical and industrial applications. 相似文献
10.
A green and efficient method for the synthesis of 2,4,5-triarylimidazoles by one-step condensation reaction of benzil, aromatic aldehyde, and ammonium acetate under catalyst-free, solvent-free, and microwave-irradiation conditions is reported. This method had many dramatic advantages, such as the short reaction time (3–5 min), good yields (80–99%), environmental friendliness, and convenient operation. 相似文献