32166-29-3Relevant academic research and scientific papers
α-Arylation and Ring Expansion of Annulated Cyclobutanones: Stereoselective Synthesis of Functionalized Tetralones
Chang, Stanley,Holmes, Michael,Mowat, Jeffrey,Meanwell, Michael,Britton, Robert
, p. 748 - 752 (2017)
α-Arylcyclobutanones display unique reactivity that makes them valuable synthetic intermediates and target molecules. We describe the preparation of α-aryl- and α-heteroarylcyclobutanones through a direct α-arylation reaction. Problematic fragmentations are avoided by the use of LiOtBu, which promotes a rapid but reversible self-aldol reaction that slowly releases the enolate required for α-arylation. We also demonstrate the ring expansion of α-arylcyclobutanones, a process that is highlighted in the stereoselective synthesis of 1-methoxy coniothyrinone D.
Deuterium kinetic isotope effects and mechanism of the thermal isomerization of bicyclo[4.2.0]oct-7-ene to 1,3-cyclooctadiene
Baldwin, John E.,Gallagher, Sarah S.,Leber, Phyllis A.,Raghavan, Anuradha S.,Shukla, Rajesh
, p. 7212 - 7219 (2004)
The thermal conversion of cis-bicyclo[4.2.0]oct-7-ene to cis,cis-1,3-cyclooctadiene might involve a direct disrotatory ring opening, or it might possibly take place by way of cis,trans-1,3-cyclooctadiene. This cis,trans-diene might possibly form the more stable cis,cis isomer through a [1,5] hydrogen shift or a trans-to-cis isomerization about the trans double bond. Deuterium kinetic isotope effect determinations for the isomerizations of 2,2,5,5-d4-bicyclo[4.2.0]oct-7-ene and 7,8-d2-bicyclo[4.2. 0]-oct-7-ene rule out these two alternatives because the observed effects are much smaller than would be anticipated for these mechanisms: k H/kD(d4) at 250 °C is 1.17 (1.04 per D), and kH/kD(d2) at 238 °C is 1.20 (1.10 per D). The direct disrotatory ring opening route remains the preferred mechanism.
Copper-Catalyzed Intermolecular Heck-Like Coupling of Cyclobutanone Oximes Initiated by Selective C?C Bond Cleavage
Zhao, Binlin,Shi, Zhuangzhi
supporting information, p. 12727 - 12731 (2017/09/08)
The first example of intermolecular olefination of cyclobutanone oximes with alkenes via selective C?C bond cleavage leading to the synthesis of nitriles in the presence of a cheap copper catalyst is reported. The procedure is distinguished by mild and safe reaction conditions that avoid ligand, oxidant, base, or toxic cyanide salt. A wide scope of cyclobutanones and olefin coupling components can be used without compromising efficiency and scalability. The alternative visible-light-driven photoredox process for this coupling reaction was also uncovered.
Direct syntheses of spiro- and fused-hydrofurans by a tunable tandem semipinacol rearrangement/oxa-michael addition protocol
Li, Bao-Sheng,Liu, Wen-Xing,Zhang, Qing-Wei,Wang, Shao-Hua,Zhang, Fu-Min,Zhang, Shu-Yu,Tu, Yong-Qiang,Cao, Xiao-Ping
supporting information, p. 5246 - 5249 (2013/05/22)
A highly chemoselective one-pot reaction has been developed involving a tandem semipinacol rearrangement/oxa-Michael addition sequence in which the in situ generated ketol diene intermediate can be transformed specifically to either the spiro- or fused-dihydrofuran products (see scheme). This one-pot tandem reaction represents a general synthetic methodology for the syntheses of the two different kinds of furan derivatives. Copyright
Baeyer-Villiger Oxidation of Cyclobutanones with 10-Methylacridinium as an Efficient Organocatalyst
Xu, Hua-Jian,Zhu, Feng-Fei,Shen, Yong-Ya,Wan, Xin,Feng, Yi-Si
experimental part, p. 4145 - 4151 (2012/07/27)
Baeyer-Villiger oxidation of cyclobutanones is achieved in current developed protocol with 10-methylacridinium perchlorate (AcrH +ClO4-) as a novel organocatalyst both with irradiation at room temperature and without irradiation at elevated temperature. Excellent yields of the corresponding lactones are obtained and the possible mechanism has been proposed.
Bicyclic nucleoside synthesis - A photochemical approach
Lee-Ruff,Wells
, p. 484 - 494 (2008/09/21)
The synthesis of a series of bicyclic nucleosides using photolytic ring-expansion of cyclobutanones is reported. The cyclobutanone precursors were prepared by [2+2] cycloaddition of a series of cyclic alkenes with chlorinated ketenes, derived from dichloro- and trichloroacetyl chloride. The synthesis of the nucleosides was achieved through photolysis of cyclobutanone precursors with 6-chloropurine by UV irradiation. The generality of this method was investigated and the absolute stereochemistry was assigned by NMR spectroscopy. The photoproducts demonstrated a marked preference for the 2′-exo conformation. Copyright Taylor & Francis Group, LLC.
Fused bicyclic or tricyclic amino acids
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, (2008/06/13)
The compounds of the instant invention are bicyclic or tricyclic amino acids useful in the treatment of epilepsy, faintness attacks, hypokinesia, cranial disorders, neurodegenerative disorders, depression, anxiety, panic, pain, arthritis, neuropathological disorders, sleep disorders, visceral pain disorders, and gastrointestinal disorders. Processes for the preparation of the final products and intermediates useful in the process are included. Pharmaceutical compositions containing one or more of the compounds are also included.
Free radical-based annulation of alkenes yielding fused cycloheptanones
Zhang, Wei,Hua, Ye,Hoge, Garrett,Dowd, Paul
, p. 3865 - 3868 (2007/10/02)
Stereospecific annulation of cyclic alkenes for the preparation of cis-fused seven-membered ring systems was accomplished by sequential [2+2] cycloaddition, exo-allylation, hydrohalogenation, and free radical ring expansion. The new strategy extends our recently developed cyclobutanone-based ring expansion reactions.
Facile activation of zinc. Preparation of cyclobutanones via dichloroketene and cyclopropanes using the Simmons-Smith reaction
Stenstrom
, p. 2801 - 2810 (2007/10/02)
Zinc powder activated by heating in an inert atmosphere gave good yields when used for the title reactions. The very easy work up procedure for the cyclobutanones further increases the potential of the method.
STRATEGY FOR CYCLOPENTENONE ANNULATION OF OLEFINS: A GENERAL PROTOCOL FOR BICYCLOENONE SYNTHESIS
Mehta, Goverdhan,Rao, K. Srinivas
, p. 1839 - 1842 (2007/10/02)
Several bicyclic α-chloro enones obtained through Greene annulation of cyclic olefins are shown to undergo efficient, two step, enone transposition via Luche reduction and aq. formic acid treatment.Application of this methodology to the formal synthesis of exaltone and (+/-)-muscone is described.
