101113-68-2Relevant academic research and scientific papers
Pseudo Vilsmeier reagents a new protocol for regiospecific C-C bond formation in pyridines
Yu, Chu-Yi,Taylor, David L.,Meth-Cohn, Otto
, p. 6661 - 6664 (1999)
2-Fluoro- and 2,6-difluoropyridine are readily quaternised with methyl p-toluenesulfonate and methyl triflate respectively. These salts readily undergo substitution of fluorine by enamines, the difluoro-derivatives being capable of specific mono- or disubstitution in a symmetrical or unsymmetrical manner. The products reduced to give keto-1, 2, 3, 6-tetrahydropyridines, can be hydrosed to the corresponding ketopyridines or hydrogenated to give ketopiperidines.
Iron-catalyzed oxyfunctionalization of aliphatic amines at remote benzylic C-H sites
Mbofana, Curren T.,Chong, Eugene,Lawniczak, James,Sanford, Melanie S.
, p. 4258 - 4261 (2016/09/09)
We report the development of an iron-catalyzed method for the selective oxyfunctionalization of benzylic C(sp3)-H bonds in aliphatic amine substrates. This transformation is selective for benzylic C-H bonds that are remote (i.e., at least three carbons) from the amine functional group. High site selectivity is achieved by in situ protonation of the amine with trifluoroacetic acid, which deactivates more traditionally reactive C-H sites that are α to nitrogen. The scope and synthetic utility of this method are demonstrated via the synthesis and derivatization of a variety of amine-containing, biologically active molecules.
ALKALOIDS OF SOME EUROPEAN AND MACARONESIAN SEDOIDEAE AND SEMPERVIVOIDEAE (CRASSULACEAE)
Stevens, Jan F.,Hart, Henk 't,Hendriks, Henk,Malingre, Theo M.
, p. 3917 - 3924 (2007/10/02)
Some 22 pyrrolidine and piperidine alkaloids were detected in the leafy parts of Sedum acre, S. aetnense, S. anglicum, S. brissemoreti, S. farinosum, S. fusiforme, S. lancerottense, S. melanantherum, and S. nudum.In addition to the alkaloids known from S. acre, 1-(2-pyrrolidyl)-propan-2-one and 2-monosubstituted piperidine alkaloids bearing butan-2-one, butan-2-ol, pentan-2-one and pentan-2-ol sidechains were identified.Phenylethylamine was isolated from the vegetative parts of S. album.In S. lydium, S. meyeri-johannis, and 16 species of S. series Rupestria, Aeonium, Greenovia, Jovibarba and Sempervivum no alkaloids could be detected.The results indicate a correlation between the presence of alkaloids and the major evolutionary trends in the European and Macaronesian Crassulaceae. Key Word Index: Sedum; Aeonium; Greenovia; Jovibarba; Sempervivum; Crassulaceae; pyrrolidine and piperidine alkaloids; chemotaxonomy; evolution.
Alkynylation of Thiolactams. New Synthesis of α-Substituted Pyrrolidine and Piperidine Alkaloids
Takahata, Hiroki,Takahashi, Koichi,Wang, Eng-Chi,Yamazaki, Takao
, p. 1211 - 1214 (2007/10/02)
Alkynylation of S-alkylthioamidium salts of thiolactams with lithium acetylides followed by reduction with LiAlH4 provided α-alkynylazacycloalkanes, which on reduction, or hydroboration followed by oxidation, gave α-substituted pyrrolidine and piperidine alkaloids.
Synthesis of (+/-)-Allosedamine by Iodide Treatment of Isoxazolidinium Salts
Liguori, Angelo,Ottana, Rosaria,Romeo, Giovanni,Sindona, Giovanni,Uccella, Nicola
, p. 2019 - 2020 (2007/10/02)
A simple stereospecific route to the (+/-)-allosedamine alkaloid has been accomplished by ring opening of the isoxazolidinium salt 2 with lithium iodide. - Key Words: (+/-)-Allosedamine / 1,3-Dipolar cycloaddition / Five-membered ring opening / Isoxazolid
A NOVEL OXIDATIVE RING-OPENING REACTION OF ISOXAZOLIDINES: SYNTHESES OF β-AMINO KETONES AND β-AMINO ACID ESTERS FROM SECONDARY AMINES
Murahashi, Shun-Ichi,Kodera, Yoichi,Hosomi, Tatsuhide
, p. 5949 - 5952 (2007/10/02)
A novel oxidative ring-opening reaction of isoxazolidines upon treatment with an electrophile and subsequently with a base gives β-amino ketones and β-amino acid esters highly efficiently.
