49812-31-9Relevant academic research and scientific papers
Radical Annulation of 2-Cyanoaryl Acrylamides via C=C Double Bond Cleavage: Access to Amino-Substituted 2-Quinolones
Xia, Wen-Jin,Fan, Tai-Gang,Zhao, Zhi-Wei,Chen, Xin,Wang, Xiang-Xiang,Li, Ya-Min
supporting information, p. 6158 - 6163 (2021/08/18)
A novel annulation of 2-cyanoaryl acrylamides via C=C double bond cleavage has been developed for facile and efficient access to a broad spectrum of functionalized 4-amino-2-quinolones, which are important N-heterocycles. In this transformation, the solvent THF is demonstrated to play a crucial role, and the addition of alkyl radicals to nitrile, 1,5-hydride shift, and cleavage of the C-C bond are involved in the mechanism.
Lewis acid-mediated reactions of 1-cyclopropyl-2-arylethanone derivatives with allenic ester, ethyl acetoacetate, and methyl acrylate
Shi, Min,Tang, Xiang-Ying,Yang, Yong-Hua
, p. 5311 - 5318 (2008/12/20)
(Chemical Equation Presented) TMSOTf-mediated reactions of 2-aryl-1-(1-phenylcyclopropyl)ethanones 1 with allenic esters afford a novel method for the synthesis of 6-methyl-3a,7-diaryl-3,3a-dihydro-2H-benzofuran-4- one derivatives 2 in moderate yields. In addition, we also found that TMSOTf-mediated reactions of 1-cyclopropyl-2-arylethanones with ethyl acetoacetate can provide the corresponding 2,3-dihydrobenzofuran-4-ol and dihydrofuro[2,3-h]chromen-2-one in moderate yields via a sequential reaction involving a nucleophilic ring-opening reaction of the cyclopropane by H 2O, one intermolecular aldol type reaction and two intramolecular aldol type reactions, a cyclic transesterification, dehydration, and aromatization. Moreover, by using methyl acrylate to replace allenic ester, the corresponding 7-aryl-3,5,6,7-tetrahydro-2H-benzofuran-4-one and 5-aryl-3,5,6,7-tetrahydro-2H-benzofuran-4-one can be formed in moderate to high yields in the presence of Bi(OTf)2Cl. Plausible reaction mechanisms have also been provided on the basis of control experiments.
Structure-activity relationship of anti-malarial spongean peroxides having a 3-methoxy-1,2-dioxane structure
Kawanishi, Motoyuki,Kotoku, Naoyuki,Itagaki, Sawako,Horii, Toshihiro,Kobayashi, Motomasa
, p. 5297 - 5307 (2007/10/03)
In order to study the structure-activity relationship of anti-malarial spongean peroxides, several analogues concerning with the 6-methoxyacetyl moiety and the 3-pentyl residue in methyl 2-(3-methoxy-3-pentyl-1,2-dioxan-6-yl) acetate were synthesized and evaluated for anti-malarial activity. In order to study the structure-activity relationship of anti-malarial spongean peroxides, several analogues concerning with the 6-methoxyacetyl moiety and the 3-pentyl residue in methyl 2-(3-methoxy-3-pentyl-1,2-dioxan-6-yl)acetate were synthesized and evaluated for anti-malarial activity. The tert-butyl ester analogue 14 showed stability in mouse serum and a high selectivity index against the malaria parasite, Plasmodium falciparum, and the citronellyl analogue 31 exhibited the strongest in vitro anti-malarial activity among them, and the imidazole analogue 25 showed desirable in vivo anti-malarial activity against P. berghei infected mice.
Intramolecular meta photocycloaddition of conformationally restrained 5-phenylpent-1-enes. Part II: Steric and electronic effects caused by 4-mono- and 4-disubstitution
Barentsen, Helma M.,Sieval, Alex B.,Cornelisse, Jan
, p. 7495 - 7520 (2007/10/02)
The meta photocycloaddition of 4-substituted 5-phenylpent-1-enes. 10-18, has been studied. The monosubstituted derivatives always prefer 2,6 addition, independent of the size of the substituent. For 2,6 addition two basic conformations are possible. Disubstituted compounds yield predominantly 1,3 addition with the sterically more demanding group exo. Except for the methoxymethyl and THF derivative the oxygen is found exo as a result of repulsion, while the monohydroxy derivative gives also endo which might be explained by hydrogen bonding. The products from compound 11 change from mainly endo-OH in cyclohexane to chiefly exo-OH in methanol. Much similarity is found with Diels-Alder cycloaddition.
The Preparation of (α-Alkylidene)tetrahydrofuran by Tungsten Catalyzed Decarboxylation of Aldol Precursors
Tanzawa, Tomoya,Schwartz, Jeffrey
, p. 6783 - 6786 (2007/10/02)
A series of substituted (α-alkylidene)tetrahydrofurans was prepared by tungsten catalyzed reaction of substituted hydroxyfuroic acids.These reactions likely involve β-lactone intermediates which decarboxylate under the reaction conditions, and rates for o
