5049-51-4Relevant academic research and scientific papers
Synthesis of Substituted Anilines from Cyclohexanones Using Pd/C-Ethylene System and Its Application to Indole Synthesis
Maeda, Katsumi,Matsubara, Ryosuke,Hayashi, Masahiko
supporting information, p. 1530 - 1534 (2021/03/08)
The synthesis of anilines and indoles from cyclohexanones using a Pd/C-ethylene system is reported. A simple combination of NH4OAc and K2CO3 under nonaerobic conditions was found to be the most suitable to perform this reaction. Hydrogen transfer between cyclohexanone and ethylene generates the desired products. The reaction tolerates a variety of substitutions on the starting cyclohexanones.
Enamines as Surrogates of Alkene Carbanions for the Reductive Alkenylation of Secondary Amides: An Approach to Allylamines
Wang, Ai-E,Yu, Cun-Cun,Chen, Ting-Ting,Liu, Yong-Peng,Huang, Pei-Qiang
supporting information, p. 999 - 1002 (2018/02/23)
A new strategy to construct allylamines through reductive alkenylation of secondary amides with enamines is reported. The method features the use of trifluoromethanesulfonic anhydride as an activation reagent of amides, and enamines as unconventional alkenylation reagents. In this manner, enamines serve as surrogates of alkene carbanions instead of the classical enolates equivalents. A possible mechanism involving a Hoffmann-like elimination of the amine-borane complex intermediate is proposed.
High-performance hypoiodite/hydrogen peroxide catalytic system for the oxylactonization of aliphatic γ-oxocarboxylic acids
Uyanik, Muhammet,Suzuki, Daisuke,Watanabe, Mizu,Tanaka, Hiroyasu,Furukawa, Kikuo,Ishihara, Kazuaki
supporting information, p. 387 - 389 (2015/03/30)
Highly efficient hypoiodite-catalyzed oxylactonization of aliphatic γ-oxocarboxylic acids to the corresponding γ-acyl-γ-butyrolactones was developed. Highly dilute reaction conditions and slow addition of the oxidant are both highly effective for promotin
New, general, and practical enamine cyclopropanation using dichloromethane
Tsai, Chia-Chung,Hsieh, I.-Lin,Cheng, Tsung-Ting,Tsai, Ping-Kuei,Lin, Kuo-Wei,Yan, Tu-Hsin
, p. 2261 - 2263 (2007/10/03)
Dichloromethane serves as a novel electrophilic carbene equivalent which adds to an enamine double bond. The presence of other alkene moieties in the enamine partner is well tolerated. Even enamines derived from sterically hindered ketones react readily with dichloromethane promoted by TiCl 4-Mg.
Facile synthesis of oxatricyclic systems with various ring sizes and substituents
Muthusamy, Sengodagounder,Arulananda Babu, Srinivasarao,Gunanathan, Chidambaram,Suresh, Eringathodi,Dastidar, Parthasarathi,Vir Jasra, Raksh
, p. 6307 - 6318 (2007/10/03)
A series of α-diazo carbonyl compounds having cyclopentanone, cyclohexanone and substituted cyclohexanone units with different tether lengths have been synthesized using diazomethane solution or methanesulphonyl azide. The above synthesized α-diazo carbon
Synthesis of juvenile hormone bioanalogs derived from 2-(4-hydroxybenzyl)-6-methylcyclohexanone
Rejzek, Martin,Zarevucka, Marie,Wimmer, Zdenek,Vanek, Tomas,Tykva, Richard,Kuldova, Jelena,Saman, David,Bennettova, Blanka
, p. 605 - 614 (2007/10/03)
A new simple approach to isomeric 2-(4-alkoxybenzyl)-6-methylcyclohexanones and the corresponding alcohols and a subsequent synthesis of compounds imitating the action of the insect juvenile hormones is described. Biological activity of the isomeric juven
Synthesis and structure-activity relationships of juvenoids derived from 2-(4-hydroxybenzyl)cycloalkan-1-ones
Rejzek,Wimmer,Saman,Ricankova,Nemec
, p. 1241 - 1255 (2007/10/02)
Juvenoids 16-30, 32, 36, 38-41, 44-46, and 49-56 containing carbamate, carbonate, and urea moieties in the molecule were synthesized and subjected to a biological screening. Carbamate juvenoids 1-4 were used as reference compounds for a detailed structure-activity study of their analogues. A clear relationship between the nature of the side chain functional group and the biological activity was found. Surprisingly, not only the juvenoids 1,4 but also 38-41, the compounds with a reversed carbamate N,O-substitution pattern, showed very promising biological activity. In contrast, the carbonate and urea derivatives displayed a remarkably low activity. The relationship between the size and substitution at atoms C(2) and C(3) of the saturated ring and the biological activity is very complex and is still not completely understood.
178. Stereoselectivity of the Radical Reductive Alkylation of Enamines: Importance of the Allylic 1,3-Strain Model
Schubert, Serge,Renaud, Philippe,Carrupt, Pierre-Alain,Schenk, Kurt
, p. 2473 - 2489 (2007/10/02)
Radical addition to enamines using Bu3SnH as reducing agent are reported (Schemes 2 and 4).The diastereoselectivity of these reactions was examined in different systems (Tables 1 and 2).Enamines derived from cyclic ketones such as cyclohexanone were alkyl
REGIOSPECIFIC SYNTHESIS OF α-ARYLSULFONOXY KETONES FROM KETONE DERIVATIVES
Hoffman, Robert V.,Carr, C. Sean
, p. 5811 - 5812 (2007/10/02)
Isomeric enol ester, enamine, and silyl enol ether derivatives of unsymmetrical ketones are converted regiospecifically to α-arylsulfonoxy ketones with arylsulfonyl peroxides.
