110729-74-3Relevant academic research and scientific papers
Synthesis of Functionalized Benzo[b]furans via Oxidative Cyclization of o-Cinnamyl Phenols
Rehan, Mohammad,Nallagonda, Rajender,Das, Braja Gopal,Meena, Tannu,Ghorai, Prasanta
supporting information, p. 3411 - 3424 (2017/04/13)
Disclosed herein is an efficient synthetic route for the synthesis of functionalized 2-benzyl benzo[b]furans via a regioselective 5-exo-trig intramolecular oxidative cyclization of ortho-cinnamyl phenols using [PdCl2(CH3CN)2] as catalyst and benzoquinone as an oxidant. Further, a sequential ortho-cinnamylation of phenols using cinnamyl alcohols catalyzed by Re2O7, followed by an oxidative cyclization using the above Pd catalyst, is performed. The reaction showed broad substrate scope with good to excellent yields.
Nucleophilic addition of α-(dimethylsilyl)nitriles to aldehydes and ketones
Jinzaki, Takaaki,Arakawa, Mitsuru,Kinoshita, Hidenori,Ichikawa, Junji,Miura, Katsukiyo
supporting information, p. 3750 - 3753 (2013/08/23)
α-Alkylated (dimethylsilyl)acetonitriles (Me2HSiCR 3R4CN) react spontaneously with aldehydes in DMSO to give β-hydroxynitriles in good to high yields. The addition to ketones is effectively promoted by using MgCl2/su
N-Heterocyclic carbene-catalyzed cyanomethylation of aldehydes with TMSAN
Fan, Ye-Cheng,Du, Guang-Fen,Sun, Wan-Fu,Kang, Wei,He, Lin
supporting information; experimental part, p. 2231 - 2233 (2012/05/20)
N-Heterocyclic carbenes (NHCs) have been served as efficient catalysts for cyanomethylation of carbonyl compounds. In the presence of 5 mol % NHC, various aldehydes and 2,2,2-trifluoroacetophenone reacted with trimethylsilylacetonitrile (TMSAN) to give β-hydroxynitriles in moderate to high yields.
P(i-PrNCH2CH2)3N as a Lewis base catalyst for the synthesis of β-hydroxynitriles using TMSAN
Wadhwa, Kuldeep,Verkade, John G.
experimental part, p. 5683 - 5686 (2009/12/06)
(Equation Presented) Proazaphosphatrane 1a was found to be an efficient catalyst for synthesis of β-hydroxynitriles via the reaction of trimethylsilylacetonitrile (TMSAN) with aldehydes under mild reaction conditions and typically low catalyst loading (ca. 2 mol %). A variety of functional groups were tolerated, and good to excellent product yields were obtained.
Optimization of 1H-tetrazole-1-alkanenitriles as potent orally bioavailable growth hormone secretagogues
Hernandez, Andres S.,Swartz, Stephen G.,Slusarchyk, Dorothy,Yan, Mujing,Seethala, R. Krishna,Sleph, Paul,Grover, Gary,Dickinson, Kenneth,Giupponi, Leah,Harper, Timothy W.,Humphreys, W. Griffith,Longhi, Daniel A.,Flynn, Neil,Murphy, Brian J.,Gordon, David A.,Biller, Scott A.,Robl, Jeffrey A.,Tino, Joseph A.
, p. 2067 - 2072 (2008/12/21)
1H-Tetrazole-1-alkanenitrile SR-9g exhibits a >10-fold in vivo potency enhancement over the lead nitrile 1 and has acceptable oral bioavailability in rats and dogs. An enantiospecific synthesis of 1H-tetrazole-1-alkanenitrile nitriles 9 has been developed.
RhI-catalyzed aldol-type reaction of organonitriles under mild conditions
Goto, Akihiro,Endo, Kohei,Ukai, Yu,Irle, Stephan,Saito, Susumu
, p. 2212 - 2214 (2008/12/22)
An aldol-type reaction of organonitriles with aldehydes was catalyzed by a RhI(OR) species under ambient conditions, and the reaction displayed a broad substrate scope with respect to both organonitrile and aldehyde components. The Royal Societ
Catalytic cyanomethylation of carbonyl compounds and imines with highly basic phosphine
Matsukawa, Satoru,Kitazaki, Eri
, p. 2982 - 2984 (2008/09/20)
A highly basic phosphine, tris(2,4,6-trimethoxy phenyl)phosphine (TTMPP), catalyzes cyanomethylation using trimethylsilylacetonitrile (TMSCH2CN) to give the corresponding products in good to high yields, with both carbonyl compounds and imines.
Catalytic nucleophilic activation of acetonitrile via a cooperative catalysis of cationic Ru complex, DBU, and NaPF6
Kumagai, Naoya,Matsunaga, Shigeki,Shibasaki, Masakatsu
, p. 8598 - 8608 (2008/02/10)
The development of an efficient catalytic system for the direct addition of acetonitrile under mild amine basic conditions is described. A cooperative catalysis of CpRu complex, DBU, and NaPF6 enables chemoselective and catalytic generation of
Efficient nickel catalyst for coupling of acetonitrile with aldehydes
Fan, Lei,Ozerov, Oleg V.
, p. 4450 - 4452 (2007/10/03)
A Ni complex of a diarylamido-based PNP ligand is an efficient and robust catalyst for coupling of acetonitrile with aldehydes. The Royal Society of Chemistry 2005.
Lewis base-catalyzed cyanomethylation of carbonyl compounds with (trimethylsilyl)acetonitrile
Kawano, Yoshikazu,Kaneko, Nobuya,Mukaiyama, Teruaki
, p. 1508 - 1509 (2007/10/03)
Catalytic cyanomethylation of various carbonyl compounds with (trimethylsilyl)acetonitrile (TMSCH2CN) in the presence of Lewis bases such as cesium or lithium acetate proceeded smoothly to afford the corresponding cyanomethylated adducts in good yields. Copyright
