Topic
Bicyclic molecule
About: Bicyclic molecule is a research topic. Over the lifetime, 29587 publications have been published within this topic receiving 451252 citations. The topic is also known as: bicyclic molecule.
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TL;DR: The palladium(0)-catalyzed cross-coupling reaction of alkynylstannanes with 2-bromoanilines or 2-trifloxyanilines results in the formation of 2-alkynylanilines.
Abstract: The palladium(0)-catalyzed cross-coupling reaction of alkynylstannanes with 2-bromoanilines or 2-trifloxyanilines results in the formation of 2-alkynylanilines. The coupling reaction tolerates substituents on the anilines, including ester, ether, chloro, and trifloxy groups. A palladium(II)-catalyzed intramolecular cyclization provides 2-substituted indoles. The cyclization proceeds without the need to reoxidize the metal and is most efficient with aliphatic substituents on the alkynyl terminus.
145 citations
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TL;DR: In this paper, a two-stage, one-flask operation using NaBH4/2-propanol, then acetic acid was used to convert phthalimides to primary amines.
144 citations
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TL;DR: In this paper, the reaction of 2-allylanilines with CO/H2 using the catalytic system Pd(OAc)2/PPh3, while use of 1,4-bis(diphenylphosphino)butane instead of PPh3 in the latter process results in the formation of the seven-membered ring lactams benzazepinones in good yield.
Abstract: 2-Allylphenols react with carbon monoxide and hydrogen in the presence of catalytic quantities of a cationic palladium(II) complex [(PCy3)2Pd(H)(H2O)]+BF4- or palladium acetate and 1,4-bis(diphenylphosphino)butane, affording five- or seven-membered ring lactones (bicyclic, tricyclic, and pentacyclic) as the principal products, often in excellent yields. Use of 2-aminostyrenes as reactants and catalytic quantities of palladium acetate and tricyclohexylphosphine, affords five-membered ring lactams in high yield and selectivity. Bicyclic and tricyclic heterocycles containing six-membered ring lactams can be synthesized from the reaction of 2-allylanilines with CO/H2 using the catalytic system Pd(OAc)2/PPh3, while use of 1,4-bis(diphenylphosphino)butane instead of PPh3 in the latter process results in the formation of the seven-membered lactams benzazepinones in good yield. The regiochemical control depends on the nature of the palladium catalyst, the relative pressures of the gases, and the solvent.
143 citations
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TL;DR: Gene-inactivation studies point to the involvement of OxyB in catalyzing the first oxidative phenol coupling reaction during glycopeptide antibiotic biosynthesis, and OxyB exhibits the typical P450-fold.
143 citations
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143 citations