695-70-5Relevant academic research and scientific papers
An efficient method for the synthesis of 2′,3′-nonsubstituted cycloalkane-1,3-dione-2-spirocyclopropanes using (2-bromoethyl)-diphenylsulfonium trifluoromethanesulfonate
Nambu, Hisanori,Ono, Naoki,Hirota, Wataru,Fukumoto, Masahiro,Yakura, Takayuki
, p. 1763 - 1768 (2016/12/09)
An efficient and practical synthesis of 2′,3′-nonsubstituted cyclohexane-1,3-dione-2-spirocyclopropanes using a sulfonium salt was achieved. The reaction of 1,3-cyclohexanediones and (2-bromoethyl)diphenylsulfonium trifluoromethanesulfonate with powdered K2CO3 in EtOAc at room temperature (r.t.) provided the corresponding spirocyclopropanes in high yields. The synthetic method was also applied to 1,3-cyclopentanedione, 1,3-cycloheptanedione, 1,3-indanedione, acyclic 1,3-diones, ethyl acetoacetate, and Meldrum's acid.
Synthesis and structural characterization of (CH2)n-bridged indenyl-pyrazoles and their cyclopentadienyl nickel(II) complexes
Tan, Weiqiang,Yu, Zhengkun,Liu, Bing,Wu, Kaikai,Liu, Zishuang,Chen, Jinzhu
scheme or table, p. 199 - 206 (2009/04/13)
A new class of (CH2)n-bridged indenyl-pyrazoles [4-{Ind-(CH2)n}-RR′PzH] (Ind = 1H-inden-3-yl, n = 1-3, RR′Pz = 3,5-disubstituted pyrazolato) were synthesized. Reactions of the indenyl-functionalized pyrazoles wi
Observations in the synthesis of the core of the antitumor illudins via an enyne ring closing metathesis cascade
Movassaghi, Mohammad,Piizzi, Grazia,Siegel, Dustin S.,Piersanti, Giovanni
scheme or table, p. 5489 - 5492 (2010/01/11)
Observations concerning the synthesis of the core spirocyclic AB-ring system of illudins using an enyne ring closing metathesis (EYRCM) cascade are discussed. Substituent effects, in addition to optimization of the reaction conditions and the olefin tethe
Enantioselective total synthesis of (-)-acylfulvene and (-)-irofulven
Siegel, Dustin S.,Piizzi, Grazia,Piersanti, Giovanni,Movassaghi, Mohammad
scheme or table, p. 9292 - 9304 (2010/03/04)
(Chemical Equation Presented) We report our full account of the enantioselective total synthesis of (-)-acylfulvene (1) and (-)-irofulven (2), which features metathesis reactions for the rapid assembly of the molecular framework of these antitumor agents. We discuss (1) the application of an Evans Cu-catalyzed aldol addition reaction using a strained cyclopropyl ketenethioacetal, (2) an efficient enyne ring-closing metathesis cascade reaction in a challenging setting, (3) the reagent IPNBSH for a late-stage reductive allylic transposition reaction, and (4) the final RCM/dehydrogenation sequence for the formation of (-)-acylfulvene (1) and (-)-irofulven (2).
Imidazolium salts as phase transfer catalysts for the dialkylation and cycloalkylation of active methylene compounds
Muthusamy, Sengodagounder,Gnanaprakasam, Boopathy
, p. 635 - 638 (2007/10/03)
The efficient synthesis of 1,1-disubstituted derivatives and the construction of cyclopropane and cyclopentane ring systems via dialkylation and cycloalkylation reactions of active methylene compounds using imidazolium salts as phase transfer catalyst is described. The dialkylation and cycloalkylation reactions of active methylene compounds in the presence of readily available imidazolium salts (ionic liquids) as phase transfer catalysts were performed to afford the respective dialkylated or cycloalkylated products. This method is very efficient for the synthesis of 1,1-disubstituted derivatives and cyclopropane and cyclopentane ring systems in a facile manner.
Microwave assisted phase transfer catalysis: An efficient solvent free method for the synthesis of cyclopropane derivatives
Gumaste,Khan, Asgar J.,Bhawal,Deshmukh
, p. 420 - 422 (2007/10/03)
Microwave assisted solvent free synthesis of cyclopropane derivatives 2a-e starting from active methylene compounds 1a-e and 1,2-dibromoethane under phase transfer conditions is described.
Electrosynthesis of cyclopropane derivatives by a Perkin-type reaction
Petrosyan, V. A.,Vasil'ev, A. A.,Tatarinova, V. I.
, p. 84 - 88 (2007/10/02)
Electrolysis of active methylene compounds at a Pt cathode in MeCN in the presence of vicinal dihaloalkanes leads to cyclopropane derivatives in yields up to 90percent.In the cases of CH-acids with low pKa it is expedient to apply more active dihaloalkanes, while for CH-acids with higher pKa the desired product yields may be raised using electrogenerated bases. - Key words: CH-acids; 1,2-dihaloalkanes; cyclopropanes; electrosynthesis; electroreduction; electronegative bases; azobenzene.
THE REACTION OF DIPHENYL DISULFIDE WITH 3,3-DIACETYLPROPYL MERCURY CHLORIDE
Russell, Glen A.,Shi, Bing Zhi
, p. 33 - 38 (2007/10/02)
The enolate anion derived from (CH3CO)2CHCH2CH2HgCl undergoes cyclization with demercuration to form 1,1-diacetylcyclopropane.The presence of Ph2S2 prevents cyclization and leads to phenylthylation at carbon and at mercury.In the absence of base Ph2S2 reacts with (CH3CO)2CHCH2CH2HgCl in a photostimulated chain reaction to form (CH3CO)2CHCH2CH2SPh. Key words: Diphenyl disulfide; mercury chloride; photostimulated reaction
CATHODIC SYNTHESIS OF CYCLOPROPANE DERIVATIVES BY THE ELECTROLYSIS OF COMPOUNDS WITH AN ACTIVATED METHYLENE GROUP IN 1,2-DICHLOROETHANE
Vasil'ev, A. A.,Tatarinova, V. I.,Petrosyan, V. A.
, p. 631 - 633 (2007/10/02)
The cathodic electrolysis of compounds with an activated methylene group in 1,2-dichloroethane leads to 1,1-disubstituted cyclopropanes.The current yield of these cyclopropane derivatives depends on the CH-acidity of the starting compounds and has a maximum at pKa ca.13.
