1197-52-0Relevant academic research and scientific papers
Synthesis of the aspidosperma alkaloid Na-formyl-16-α- hydroxyaspidospermidine
Belferdi, Fatiha,Belattar, Abdelhamid
, p. 803 - 814 (2001)
The first total synthesis of Na-formyl-16α- hydroxyaspidospermidine and its isomer via (±)-vincadifformine is described and their structure elucidation using different methods of analysis is reported.
Osmium Hydride Acetylacetonate Complexes and Their Application in Acceptorless Dehydrogenative Coupling of Alcohols and Amines and for the Dehydrogenation of Cyclic Amines
Esteruelas, Miguel A.,Lezáun, Virginia,Martínez, Antonio,Oliván, Montserrat,Onate, Enrique
, p. 2996 - 3004 (2017/08/21)
The preparation of new osmium hydride complexes, starting from OsH6(PiPr3)2 (1) and OsH2Cl2(PiPr3)2 (2), and their catalytic activity in acceptorless dehydrogenative coupling of alcohols and amines and in dehydrogenation of cyclic amines are reported. Complex 1 reacts with acetylacetone (Hacac) to give the classical trihydride OsH3(acac)(PiPr3)2 (3). The protonation of 3 with triflic acid (HOTf) produces the release of H2 and the formation of the unsaturated osmium(IV) dihydride [OsH2(acac)(PiPr3)2]OTf (4), which is also prepared by starting from 2 via the intermediate OsH2Cl(acac)(PiPr3)2 (5). Treatment of an acetylacetone solution of 5 with KOH affords Os(acac)2(PiPr3)2 (6). In the presence of 5 mol % of KOH, complexes 3-6 promote the coupling of benzyl alcohol and aniline to give N-benzylideneaniline and H2. Under the same conditions, complex 3 catalyzes a wide range of analogous couplings to afford a variety of imines, including aliphatic imines, with yields between 90 and 40% after 1-48 h. Complex 3 also catalyzes the dehydrogenation of cyclic amines. According to the amount of H2 released by each 1 g of employed substrate, the amines have been classified into three classes: poor (1,2,3,4-tetrahydroquinaldine, 2-methylindoline, and 2,6-dimethylpiperidine), moderate (1,2,3,4-tetrahydroquinoline and 6-methyl-1,2,3,4-tetrahydroquinoline), and good hydrogen donors (1,2,3,4-tetrahydroisoquinoline).
Iron-Catalyzed Mild and Selective Hydrogenative Cross-Coupling of Nitriles and Amines To Form Secondary Aldimines
Chakraborty, Subrata,Leitus, Gregory,Milstein, David
supporting information, p. 2074 - 2078 (2017/02/15)
The first example of a base-metal-catalyzed homogeneous hydrogenative coupling of nitriles and amines to selectively form secondary cross-imines is reported. The reaction is catalyzed under mild conditions by a well-defined (iPr-PNP)Fe(H)Br(CO) pincer pre-catalyst and catalytic tBuOK.
Aerobic oxidative coupling of alcohols and amines towards imine formation by a dicopper(I,I) catalyst
Dutta, Indranil,De, Subhabrata,Yadav, Sudhir,Mondol, Ranajit,Bera, Jitendra K.
, p. 117 - 124 (2017/09/30)
A dicopper(I,I) complex [Cu2(L1) (Cl)2] (1), bearing a Cu2Cl2 core spanned by a naphthyridine–diimine ligand is synthesized by the treatment of CuCl with 2,7–bis(N–mesitylmethylimino)–1,8–naphthyridine (L1). The catalytic efficacy of 1 is assessed for aerobic oxidative synthesis of imines from alcohols and amines. The title complex is found to be an excellent catalyst for a wide variety of alcohols and amines. Kinetic experiments revealed the involvement of both copper ions in the aerobic oxidation process. The general utility of naphthyridine based ligands to favour a possible bimetallic pathway for a catalytic reaction is demonstrated here.
Direct access to pop-type osmium(II) and osmium(IV) complexes: Osmium a promising alternative to ruthenium for the synthesis of imines from alcohols and amines
Esteruelas, Miguel A.,Honczek, Nicole,Olivan, Montserrat,Onate, Enrique,Valencia, Marta
scheme or table, p. 2468 - 2471 (2011/06/27)
An easy and direct access to POP-type osmium(II) and osmium(IV) complexes, including OsH4{dbf(PiPr2)2} (dbf(PiPr2)2 = 4,6-bis(diisopropylphosphine) dibenzofuran), is reported. This tetrahydride derivative is an efficient catalyst for the selective formation of imines from alcohols and amines with liberation of H2, proving that osmium is a promising alternative to ruthenium for catalysis.
Discovery of substituted biphenyl imidazoles as potent, bioavailable bombesin receptor subtype-3 agonists
He, Shuwen,Dobbelaar, Peter H.,Liu, Jian,Jian, Tianying,Sebhat, Iyassu K.,Lin, Linus S.,Goodman, Allan,Guo, Cheng,Guzzo, Peter R.,Hadden, Mark,Henderson, Alan J.,Ruenz, Megan,Sargent, Bruce J.,Yet, Larry,Kelly, Theresa M.,Palyha, Oksana,Kan, Yanqing,Pan, Jie,Chen, Howard,Marsh, Donald J.,Shearman, Lauren P.,Strack, Alison M.,Metzger, Joseph M.,Feighner, Scott D.,Tan, Carina,Howard, Andrew D.,Tamvakopoulos, Constantin,Peng, Qianping,Guan, Xiao-Ming,Reitman, Marc L.,Patchett, Arthur A.,Wyvratt Jr., Matthew J.,Nargund, Ravi P.
scheme or table, p. 1913 - 1917 (2010/07/02)
We report SAR studies on a novel non-peptidic bombesin receptor subtype-3 (BRS-3) agonist lead series derived from high-throughput screening hit RY-337. This effort led to the discovery of compound 22e with significantly improved potency at both rodent and human BRS-3.
Electrochemical oxidation of benzylic amines into the corresponding imines in the presence of catalytic amounts of KI
Okimoto, Mitsuhiro,Takahashi, Yukio,Numata, Kaori,Nagata, Yuji,Sasaki, Gaku
, p. 1989 - 1995 (2007/10/03)
Oxidation of various benzylic amines using an indirect electrochemical method was successfully carried out under very mild conditions to afford the corresponding imines in good yields. Our results show that, for this electrolytic system, the iodide ions play an important role as electron carriers. Copyright Taylor & Francis, Inc.
A one-pot synthesis of tetrahydroisoquinolonic acids from aldehydes and amines in trimethylorthoformate
Yu, Niefang,Poulain, Rebecca,Gesquiere, Jean-Claude
, p. 355 - 356 (2007/10/03)
Tetrahydroisoquinolonic acids are synthesized in the presence of excess trimethyl orthoformate by a one-pot procedure directly from the corresponding amines, aldehydes and homophthalic anhydride.
REACTIONS OF N-1-(2,2-DICHLOROALKYLIDENE)AMINES WITH POTASSIUM CYANIDE: SYNTHESIS OF β-CHLORO-α-CYANOENAMINES, α-CHLOROIMIDATES AND 2-AMINO-5-CYANOPYRROLS
Verhe, Roland,Kimpe, Norbert De,Buyck, Laurent De,Tilley, Marc,Schamp, Niceas
, p. 131 - 142 (2007/10/02)
Reaction of N-1-(2,2-dichloroalkylidene)amines, prepared by chlorination of aliphatic aldimines with N-chlorosuccinimide, with excess of potassium cyanide in methanol gave β-chloro-α-cyanoenamines.When the reaction was carried out for a longer period, α-c
Vincadifformine synthesis process
-
, (2008/06/13)
The preparation of vincadifformine and some derivatives thereof for use as a starting material for synthesis of the corresponding vincamine derivatives or for synthesis of bisindole alkaloids having clinically important antitumor properties.
