6230-72-4Relevant academic research and scientific papers
Synthesis of biomimetic light-driven molecular switches via a cyclopropyl ring-opening/nitrilium ion ring-closing tandem reaction
Zanirato, Vinicio,Pollini, Gian P.,De Risi, Carmela,Valente, Filippo,Melloni, Alfonso,Fusi, Stefania,Barbetti, Jacopo,Olivucci, Massimo
, p. 4975 - 4982 (2007)
A cyclopropyl ring-opening/nitrilium ion ring-closing tandem reaction has been conveniently used in an expeditious synthetic approach to light-driven Z/E molecular switches featuring an imine function conjugated to olefin groups that mimics natural proton
Rhenium(I)-Catalyzed C-Methylation of Ketones, Indoles, and Arylacetonitriles Using Methanol
Shee, Sujan,Kundu, Sabuj
, p. 6943 - 6951 (2021/05/29)
A ReCl(CO)5/MeC(CH2PPh2)3 (L2) system was developed for the C-methylation reactions utilizing methanol and base, following the borrowing hydrogen strategy. Diverse ketones, indoles, and arylacetonitriles underwent mono-and dimethylation selectively up to 99% yield. Remarkably, tandem multiple methylations were also achieved by employing this catalytic system.
Br?nsted Base-Catalyzed Transformation of α,β-Epoxyketones Utilizing [1,2]-Phospha-Brook Rearrangement for the Synthesis of Allylic Alcohols Having a Tetrasubstituted Alkene Moiety
Kondoh, Azusa,Tasato, Naoko,Aoki, Takuma,Terada, Masahiro
supporting information, p. 5170 - 5175 (2020/07/04)
A stereoselective transformation of α,β-epoxyketones into alkenylphosphates having a hydroxymethyl group on the β-carbon was established by utilizing the [1,2]-phospha-Brook rearrangement under Br?nsted base catalysis. The reaction involves the catalytic generation of an α-oxygenated carbanion located at the α-position of an epoxide moiety through the [1,2]-phospha-Brook rearrangement and the following epoxide opening. Further transformation of the alkenylphosphates by the palladium-catalyzed cross-coupling reaction with Grignard reagents provided allylic alcohols having a stereodefined all-carbon tetrasubstituted alkene moiety.
Transition-Metal-Free Reductive Deoxygenative Olefination with CO2
Zhu, Dao-Yong,Li, Wen-Duo,Yang, Ce,Chen, Jie,Xia, Ji-Bao
, p. 3282 - 3285 (2018/06/11)
A new transition-metal-free reductive deoxygenative olefination of phosphorus ylides with CO2, an abundant and sustainable C1 chemical feedstock, is described. This catalytic CO2 fixation afforded β-unsubstituted acrylates and vinyl ketones in good yields with broad scope and good functional group tolerance under mild reaction conditions. Cost-effective and easily handled polymethylhydrosiloxane was used as a reductant. Bis(silyl)acetal was proved to be the key intermediate in this reductive functionalization of CO2.
Transition Metal-Free α-Csp3-H Methylenation of Ketones to Form C=C Bond Using Dimethyl Sulfoxide as Carbon Source
Liu, Yu-Feng,Ji, Peng-Yi,Xu, Jing-Wen,Hu, Yu-Qun,Liu, Qiang,Luo, Wei-Ping,Guo, Can-Cheng
, p. 7159 - 7164 (2017/07/26)
A direct α-Csp3-H methylenation of arylketones to form C=C bond using dimethyl sulfoxide as one-carbon source is achieved under transition metal-free reaction condition. Various aryl ketone derivatives react readily with DMSO, producing the α,β-unsaturated carbonyl compounds in yields of 42 to 90%. This method features a transition metal-free reaction condition, wide substrate scope and using DMSO as novel one-carbon source to form C=C bond, thus providing an efficient and expeditious approach to an important class of α,β-unsaturated carbonyl compounds. Based on the preliminary experiments, a plausible mechanism of this transformation is disclosed.
Nazarov cyclization of divinyl and arylvinyl epoxides: Application in the synthesis of resveratrol-based natural products
Sudhakar, Gangarajula,Satish, Kovela
supporting information, p. 6475 - 6480 (2015/04/22)
New variation in the Nazarov cyclization has been developed by preparing divinyl and arylvinyl epoxides as pentadienyl cation precursors for the first time. Highly substituted cyclopentadienes, hydrindienes, and indenes were synthesized to demonstrate the compatibility of this reaction with substrates bearing a variety of substitutions and having different types of epoxides. Application of this method in the synthesis of resveratrol-based natural products was also demonstrated.
Preparation of acrylophenones and 2-alkyl indanones utilizing hexamethylenetetramine as an inexpensive Mannich reagent
Bhattacharya, Apurba,Segmuller, Brigitte,Ybarra, Arnold
, p. 1775 - 1784 (2007/10/03)
Hexamethylenetetramine/acetic anhydride-promoted α-methylenation of aryl alkyl ketones followed by acid-catalyzed cyclization of the resulting acrylophenones produce 2-alkyl indanones in excellent yields.
Neighbouring group participation in the solvolysis of a class of heterocyclic and acyclic trans-dibromides and bromohydrins
Mandal, Asok N,Chatterjee, Amareshwar
, p. 156 - 162 (2007/10/02)
Solvolysis of heterocyclic trans-dibromides and bromohydrins 1a-e affords the ring contracted aldehydes 10a-c and the benzthiophen derivative 11.The acyclic dibromide 2a similarly provides the expected aldehyde 13.Probable pathways for the formation of the products have been presented.
Synthesis of 4-Benzoyl-4-methylcyclohexa-2,5-dienone and its Benzoyl Substitued Derivatives: Isolated 4-Acylcyclohexa-2,5-dienones
Jackson, Lorraine B.,Waring, Anthony J.
, p. 1791 - 1798 (2007/10/02)
The synthesis are reported of 4-benzoyl-4-methylcyclohexa-2,5-dienone, and its 4-(4-chlorobenzoyl) and 4-(4-methoxybenzoyl) analogues.These are the first isolated 4-acylcyclohexa-2,5-dienones containing the dienone function in a monocyclic ring system.All are sensitive to nucleophilic attack at the benzoyl carbonyl group, being cleaved to 4-methylphenol and its derivatives of the appropriate substitued benzoic acid.Treatment with acids failed to give the desired dienone-phenol rearrangement, with a benzoyl migration from C-4 to C-3, but instead gave 4-methylphenyl benzoate or its derivatives, by a reversal of a Fries rearrangement with C-4 to O-aroyl migration.
