1283152-85-1Relevant academic research and scientific papers
Phosphazene base-catalyzed hydroamination of aminoalkenes for the construction of isoindoline scaffolds: Application to the total synthesis of aristocularine
Matsuoka, Junpei,Terashita, Maki,Miyawaki, Akari,Tomioka, Kiyoshi,Yamamoto, Yasutomo
supporting information, (2021/12/30)
A method for isoindoline synthesis via phosphazene base-catalyzed intramolecular hydroamination of aminoalkenes was developed. The reaction has a broad functional group tolerance, including for halide, cyano, and methoxy groups, and could also be used to
Organoselenium-Catalyzed Aza-Wacker Reactions: Efficient Access to Isoquinolinium Imides and an Isoquinoline N -Oxide
Li, Huimin,Liao, Lihao,Zhao, Xiaodan
supporting information, p. 1688 - 1692 (2019/08/26)
An efficient approach for the organoselenium-catalyzed aza-Wacker reaction of olefinic hydrazones and an oxime to form isoquinolinium imides and an isoquinoline N -oxide is developed. This transformation involves a direct intramolecular C-H amination using hydrazones and an oxime as imine-type nitrogen sources. This work not only provides a new approach for the construction of isoquinoline derivatives, but also expands the scope of nitrogen sources in electrophilic selenium catalysis.
Rhodium-catalyzed intramolecular hydroacylation of 1,2-disubstituted alkenes for the synthesis of 2-substituted indanones
Yuan, Jing,Liu, Chong,Chen, Yan,Zhang, Zhenfeng,Yan, Deyue,Zhang, Wanbin
, p. 269 - 277 (2018/12/05)
The intramolecular hydroacylation of 1,2-disubstituted alkenes was considered to be a challenging task due to the side reactions resulted from the lack of additional substituent at 1-position and the low activity caused by the steric hindrance of substituent at 2-position, and an asymmetric version has not been considered possible due to problems associated with the racemization of the products. We have partially solved these problems. Catalyzed by an activated diphosphine-Rh complex and reacted in a selected dihalogenated solvent, the intramolecular hydroacylation of o-(2-arylvinyl)benzaldehydes provided the corresponding 2-aryl-1-indanones in high yields, and its asymmetric variant using o-(2-alkylvinyl)benzaldehydes afforded chiral 2-alkyl-1-indanones in high yields and with moderate enantioselectivities.
An investigation of the scope of the 1,7-electrocyclization of α,β:γ,δ-conjugated azomethine ylides
Zhang, Weimin,Ning, Fuqiang,Váradi, Linda,Hibbs, David E.,Platts, James A.,Nyerges, Miklós,Anderson, Rosaleen J.,Groundwater, Paul W.
supporting information, p. 3621 - 3629 (2014/05/20)
Substituents on the diene component have little influence on the periselectivity of the cyclizations of α,β:γ,δ-conjugated azomethine ylides, with 1,7-electrocyclizations predominating. In some cases, subtle changes to these substituents can, however, influence the product formed, through their effect on the relative energies of the transition states for the 1,5- (6π) and 1,7-electrocyclization (8π) processes. The most striking changes in periselectivity occur for phenylethenyl-substituted azomethine ylides 3d-f, which can give either a pyrroline 4d,f or dihydrobenzazepine 6e, depending upon the alkene configuration.
Synthesis of substituted 2-arylindanes from e -(2-stilbenyl)methanols via lewis acid-mediated cyclization and nucleophililc transfer from trialkylsilyl reagents
Sarnpitak, Pakornwit,Trongchit, Kanokrat,Kostenko, Yulia,Sathalalai, Supaporn,Gleeson, M. Paul,Ruchirawat, Somsak,Ploypradith, Poonsakdi
, p. 8281 - 8296 (2013/09/24)
A preparative method for the synthesis of functionalized 2-arylindanes has been developed via the Lewis acid-mediated ring closure of stilbenyl methanols followed by nucleophilic transfer from trialkylsilyl reagents. The reactions gave the corresponding p
AuI-catalyzed intramolecular cyclization of 2-alkenylphenyl carbonyl compounds: Exploring the oxophilic Lewis acidity of AuI species
Jagdale, Arun R.,Youn, So Won
supporting information; experimental part, p. 3904 - 3910 (2011/09/15)
A AuI-catalyzed intramolecular cyclization reaction of 2-alkenylphenyl carbonyl compounds to afford a variety of indene, indenol, and indanone ring systems was developed. In this process, AuI serves to activate the carbonyl group of β-keto esters, aldehydes, and ketones, preferentially exhibiting oxophilicity in the presence of C-C multiple bonds. Furthermore, β-keto esters could participate as the electrophilic partner in reactions with carbon nucleophile such as alkenes. Copyright
Ring-closure reactions of 1,2-diaza-4,5-benzoheptatrienyl metal compounds: Experiment and theory
Kleine, Tillmann,Bergander, Klaus,Froehlich, Roland,Wibbeling, Birgit,Wuerthwein, Ernst-Ulrich
experimental part, p. 1979 - 1991 (2011/05/07)
2-Alkenylbenzylidene hydrazones 5a-m, which are accessible in good to excellent yields in a four-step synthesis, are converted into 1,2-diaza-4,5-benzoheptatrienyl metal compounds 1a-m by treatment with KO-t-Bu as base. These metal compounds undergo the various types of reactions in good yields and exclusively depending on the nature of substituents R1 and R3. Thus, metal compounds 1a-c carrying alkyl substituents R 1 and R3 form 3H-benzodiazepines 6a-c after electrophilic quench of the intermediate cyclic anion 7 in a 7-endo-trig electrocyclic reaction with a moebius aromatic transition structure 1--TS. Similarly, a benzothienyl derivative 5n is converted into diazepine 6d. Potassium compounds 1d-h, which are N-methyl and aryl substituted at R 3, form 1,2-dihydrophthalazines 8a-e in a predominantly charge-controlled 6-exo-trig cyclization reaction. In contrast, aryl-aryl-substituted systems 5i-m did not lead to cyclic products upon deprotonation, but the intermediate open-chain metal compounds 1i-m were trapped by acid chlorides at N1 to yield the hydrazides 10a-e. We interpret thermodynamics and kinetics of these reactions in the context of the Baldwin rules on the basis of quantum chemical calculations and discuss the transition structures considering the results of NICS and NBO-charge calculations. Examples of the products 6, 8, and 10 could be characterized by X-ray diffraction.
