587882-43-7Relevant academic research and scientific papers
Syntheses of isochromenes and naphthalenes by electrophilic cyclization of acetylenic arenecarboxaldehydes
Yue, Dawei,Della Ca, Nicola,Larock, Richard C.
, p. 3381 - 3388 (2006)
Highly substituted IH-isochromenes, isobenzofurans, and pyranopyridines can be prepared by allowing o-(1-alkynyl)arenecarboxaldehydes and ketones to react with I2, ICl, NIS, Br2, NBS, p-O2NC 6H4SCl, or PhSeBr and various alcohols or carbon-based nucleophiles at room temperature. Naphthyl ketones and iodides are also readily prepared by the reaction of 2-(1-alkynyl)arenecarboxaldehydes with I2 and simple olefins or alkynes.
Efficient syntheses of heterocycles and carbocycles by electrophilic cyclization of acetylenic aldehydes and ketones
Yue, Dawei,Della Ca, Nicola,Larock, Richard C.
, p. 1581 - 1584 (2004)
Highly substituted oxygen heterocycles can be prepared in good yields at room temperature by reacting o-(1-alkynyl)-substituted arene carbonyl compounds with NBS, I2, ICI, p-O2NC6H4SCl, or PhSeBr and various alc
Cyclization of carbonyl groups onto alkynes upon reaction with IPy2BF4 and their trapping with nucleophiles: A versatile trigger for assembling oxygen heterocycles
Barluenga, Jose,Vazquez-Villa, Henar,Ballesteros, Alfredo,Gonzalez, Jose M.
, p. 9028 - 9029 (2003)
Iodonium ions liberated from bis(pyridine)iodonium(I) tetrafluoroborate react with ortho-alkynyl-substituted carbonyl compounds and different nucleophiles to give valuable iodinated heterocycles at room temperature, through a new and metal-free reaction sequence. Interestingly, the nature of the nucleophile can be widely modified, and not only alcohols but also several carbon-based nucleophiles can be nicely used. Copyright
The reaction of o-alkynylarene and heteroarene carboxaldehyde derivatives with iodonium ions and nucleophiles: A versatile and regioselective synthesis of 1H-isochromene, naphthalene, indole, benzofuran, and benzothiophene compounds
Barluenga, Jose,Vazquez-Villa, Henar,Merino, Isabel,Ballesteros, Alfredo,Gonzalez, Jose M.
, p. 5790 - 5805 (2008/03/11)
The reaction of o-alkynyl-benzaldehydes 1 with different alcohols, silylated nucleophiles 5, electronrich arenes 10, and heteroarenes 12 in the presence of the reagent IPy2BF4, at room temperature, gave functionalized 4-iodo-1H-isochromenes 2, 6, 11, and 13 in a regioselective manner. When alkynes 16 and alkenes 19 and 20 were used as nucleophiles, a regioselective benzannulation reaction took place to form 1-iodonaphthalenes 17 and 1-naphthyl ketones 18, respectively. Moreover, the latter process has been adapted to accomplish the synthesis of indole, benzofuran, and benzothiophene derivatives (23, 27, and 28, respectively). The three patterns of reactivity observed for the o-alkynylbenzaldehyde derivatives with IPy2BF 4 stem from a common iodinated isobenzopyrylium ion intermediate, A, that evolves in a different way depending on the nucleophile present in the reac-tion medium. A mechanism is proposed and the different reaction pathways observed as a function of the type of nucleophile are discussed. Furthermore, the reaction of the o-hexynyl-benzaldehyde 1b with styrene was monitored by NMR spectroscopy. Compound III, a resting state for the common intermediate in the absence of acid, has been isolated. Its evolution in acid media has been also tested, thereby providing support to the proposed mechanism.
