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A novel and efficient one-pot synthesis of spiro[indoline-3,4?- pyrazolo[3,4-b]quinoline]dione, spiro[furo[3,4-e]pyrazolo[3,4-b]pyridine-4, 3?-indoline]dione, and spiro[indeno[2,1-e]pyrazolo[3,4-b]pyridine-4, 3?-indoline]dione derivatives via three-component reaction of isatin, 5-amino-3-methylpyrazole, and 1,3-dicarbonyl compounds in aqueous medium is described. The advantages of this method include high efficiency, mild reaction conditions, convenient operation, and environmentally benign conditions.

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This review details the current methods used to prepare vinyl triflates derived from 1,3-dicarbonyl compounds and describes the reactivity of such functionalized vinyl triflates. alpha-Ketovinyl triflates can easily and stereoselectively be produced through three different ways. Enolization and triflation is the most common route, but direct triflation with triflic anhydride could also be used, each involving different mechanisms. Direct addition of triflic acid and related sulfonic acids to triple bond offers an alternative to the previous methods. With their peculiar set of functional groups, alpha-ketovinyl triflates can react in four different ways. The vinyl triflate part could be engaged in coupling reactions, while the carbonyl group as well as the enone motif could be subjected to nucleophilic additions. If a proton is available next to the triflate group, eliminations could occur under basic conditions. Upon addition, fragmentations could also be possible.

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(Chemical Equation Presented) In this study, a series of new and significative bisfunctional compounds containing two furo[3,4-b]quinoline and acridinedione skeletons has been synthesized through a rapid one-pot three-component reaction of dialdehydes with N-aryl enaminones and cyclic-1,3-dicarbonyl compounds (tetronic acid and cyclohexane-1,3-dione) in mixed solvent of glacial acetic acid and N,N-dimethylformamide under microwave irradiation without catalyst. This method has the advantages of good yield and simple workup procedure.

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Covering: Up to end of June 2018 Baeyer-Villiger monooxygenases (BVMOs) are flavin-dependent enzymes that catalyse the oxidation of ketones and cyclic ketones to esters and lactones, respectively, by using molecular oxygen and NAD(P)H. BVMOs also catalyse sulfoxidations and N-oxidations. BVMOs are widely studied as attractive biocatalysts, but also catalyse key reactions in metabolic pathways of the organisms from which they are sourced. BVMOs are involved in the primary metabolism of atypical carbon sources, thereby conferring an evolutionary advantage to the host organism. In addition, BVMOs catalyse a plethora of diverse Baeyer-Villiger and heteroatom oxidations in the construction of complex secondary metabolites. These natural products often have attractive biological properties, such as anti-bacterial, anti-cancer and anti-proliferative activity, and can have clinical applications. In contrast, BVMOs are also involved in the synthesis of microbial toxins. This review will discuss the inherent roles of type I, type II and type O BVMOs in the metabolism of microorganisms.

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A facile and efficient one-pot procedure for the preparation of functionalized dihydro-1H-indol-4(5H)-ones by a catalyst-free, three-component reaction of 1,3-dicarbonyl compounds, arylglyoxal monohydrate and enaminones under mild conditions in excellent yield is reported. This synthesis was confirmed to follow the group-assisted-purification (GAP) chemistry process, which can avoid traditional purifications, chromatography, and recrystallization.

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A mild and efficient strategy for the construction of furo[3, 2-c]pyrones via an annulation of alpha-keto vinyl azides and 4-hydroxypyrones under catalyst free condition has been described. Several furo[3, 2-c]pyrone scaffolds were synthesized from readily available vinyl azides and 4-hydroxypyrones in a regiospecific manner. This protocol allows the formation of new C?O and C?C bonds in a single step to provide a wide variety of substituted furano heterocycles. It is worth noting that the present protocol has several advantages over the conventional methods such as catalyst free, short reaction duration and operational simplicity with good yields.

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Torquoselective pericyclic ring closures of 1-azatrienes that contain acyclic chirality at the C-terminus are described herein.

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Podophyllotoxin has been extensively used as a lead agent in the development of new anticancer drugs. On the basis of the previously reported simplified 4-aza-2,3-didehydro podophyllotoxin analogues, we implemented a bioisosteric replacement of the methylenedioxybenzene subunit with a pyrazole moiety to afford tetracyclic dihydropyridopyrazoles. Libraries of these structurally simple analogues are prepared by a straightforward one-step multicomponent synthesis and demonstrated to display antiproliferative properties in a number of human cancer cell lines. These new heterocycles potently induce apoptosis in cancerous Jurkat cells even after a short 24 h exposure. In contrast, no apoptosis is detected in primary lymphocytes under the same treatment conditions. The ease of synthesis and encouraging biological activities make the presented library of dihydropyridopyrazoles promising new leads in anticancer drug design.

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A series of novel conjugates of 4-aza-2,3-didehydropodophyllotoxins (11a-w) were synthesized by a straightforward one-step multicomponent synthesis that demonstrated cytotoxicity against five human cancer cell lines (breast, oral, colon, lung and ovarian). All the twenty three compounds (11a-w) have been examined for the inhibition of tubulin polymerization. Among these compounds, 11a, 11k and 11p exhibited inhibition of polymerization tubulin comparable to podophyllotoxin apart from disruption of microtubule organization within the cells. Flow cytometric analysis showed that these compounds (11a, 11k and 11p) arrested the cell cycle in the G2/M phase of cell cycle leading to caspase-3 dependent apoptotic cell death.

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A concise and scalable enantioselective total synthesis of the natural cardenolides cannogenol and cannogenol-3-O-alpha-l-rhamnoside has been achieved in 18 linear steps. The synthesis features a Cu(II)-catalyzed enantioselective and diastereoselective Michael reaction/tandem aldol cyclization and a one-pot reduction/transposition, which resulted in a rapid (6 linear steps) assembly of a functionalized intermediate containing C19 oxygenation that could be elaborated to cardenolide cannogenol. In addition, a strategy for achieving regio- and stereoselective glycosylation at the C3 position of synthetic cannogenol was developed and applied to the preparation of cannogenol-3-O-alpha-l-rhamnoside.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem