91645-35-1Relevant academic research and scientific papers
Aza-heterocycles via copper-catalyzed, remote C–H desaturation of amines
Dare, Ross M.,Nagib, David A.,Paneque, Alyson N.,Stateman, Leah M.
, p. 210 - 224 (2022/01/19)
A majority of medicines contain a nitrogen atom within a five- or six-membered ring. To rapidly access both such aza-heterocycles, we sought to develop a remote C–H desaturation of amines. Inspired by the Hofmann-L?ffler-Freytag (HLF) synthesis of five-me
Chemoselective Intramolecular Formal Insertion Reaction of Rh–Nitrenes into an Amide Bond Over C?H Insertion
Kono, Masato,Harada, Shingo,Nemoto, Tetsuhiro
, p. 3119 - 3124 (2019/02/13)
The past few decades have witnessed extensive efforts to disclose the unique reactivity of metal–nitrenes, because they could be a powerful synthetic tool for introducing the amine functionality into unactivated chemical bonds. The reactivity of metal–nitrenes, however, is currently mainly confined to aziridination (an insertion into a C=C bond) and C?H amination (an insertion into a C?H bond). Nitrene insertion into an amide C?N bond, however, has not been reported so far. In this work we have developed a rhodium-catalyzed one-nitrogen insertion into amide C?N and sulfonamide S?N bonds. Experimental and theoretical analyses based on density functional theory indicate that the formal amide insertion proceeds via a rhodium-coordinated ammonium ylide formed between the nitrene and the amide nitrogen, followed by acyl group transfer concomitant with C?N bond cleavage. Mechanistic studies have allowed rationalization of the origin of the chemoselectivity observed between the C?H and amide insertion reactions. The methodology presented herein is the first example of an insertion of nitrene into amide bonds and provides facile access to unique diazacyclic systems with an N?N bond linkage.
M-CPBA-Mediated Intramolecular Aminohydroxylation of N-Sulfonyl Aminoalkenes to Synthesize β-Hydroxyl Cyclic Amines
Yin, Yan,Zhou, Hong,Sun, Guofeng,Liu, Xichen
, p. 1337 - 1345 (2015/10/06)
A variety of structurally diverse N-sulfonyl-protected aminoalkenes readily reacted with m-CPBA to produce a series of β-hydroxyl cyclic amines in high yields through intramolecular aminohydroxylation. This metal-free and easy-to-handle synthetic methodol
MCPBA-mediated metal-free intramolecular aminohydroxylation and dioxygenation of unfunctionalized olefins
Liu, Gong-Qing,Li, Lin,Duan, Lili,Li, Yue-Ming
, p. 61137 - 61143 (2015/08/03)
mCPBA-mediated metal-free intramolecular aminohydroxylation and dioxygenation reactions of unfunctionalized olefins are reported. In the presence of 1.2 equiv. of m-chlorobenzoic peracid, different N-sulfonyl 4-penten-1-amine substrates could be cyclized
Br?nsted acid-assisted intramolecular aminohydroxylation of N -alkenylsulfonamides under heavy metal-free conditions
Moriyama, Katsuhiko,Izumisawa, Yuta,Togo, Hideo
, p. 9846 - 9851 (2013/01/15)
The intramolecular aminohydroxylation of N-alkenylsulfonamides proceeded under heavy metal-free conditions to give substituted prolinol derivatives in high yields. Oxone activated by catalytic Br?nsted acid worked well as an electrophilic oxidant for this reaction.
Flexible gold-catalyzed regioselective oxidative difunctionalization of unactivated alkenes
De Haro, Teresa,Nevado, Cristina
supporting information; experimental part, p. 906 - 910 (2011/03/19)
AuI/AuIII catalytic cycles can trigger three highly regioselective alkene difunctionalization processes that involve the formation of C(sp3)iO, C(sp3)iN, and C(sp3)iC(sp 2) bonds. The react
Synthesis of alkaloid analogues from β-amino alcohols by β-fragmentation of primary alkoxyl radicals
Boto, Alicia,Hernandez, Dacil,Hernandez, Rosendo,Montoya, Adriana,Suarez, Ernesto
, p. 325 - 334 (2007/10/03)
The fragmentation of primary alkoxyl radicals is usually a minor process with respect to hydrogen abstraction and other competing reactions. However, when β-amino alcohols were used as substrates, the scission proceeded in good to excellent yields and no side reactions were observed. The fragmentation can be coupled with an allylation or alkylation reaction, to give alkaloid analogues and functionalized nitrogen heterocycles. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
1-sulfonyl pyrrolidine derivatives
-
, (2008/06/13)
The present invention is a series of compounds that are derivatives of 1-sulfonyl-pyrrolidine and that demonstrate affinity towards metabotropic glutamate receptors. The invention further relates to medicaments containing these compounds and to a process for their preparation. The compounds possess affinity towards metabotropic glutamate receptors and are therefore useful in the treatment or prevention of acute and/or chronic neurological disorders.
Acid-catalyzed cyclization of vinylsilanes bearing an amino group. Stereoselective synthesis of pyrrolidines
Miura, Katsukiyo,Hondo, Takeshi,Nakagawa, Takahiro,Takahashi, Tatsuyuki,Hosomi, Akira
, p. 385 - 388 (2007/10/03)
(FORMULA PRESENTED) In the presence of an acid catalyst, vinylsilanes 1 bearing an amino group protected by an electron-withdrawing group were smoothly cyclized to 2-(silylmethyl)pyrrolidines 2. This cyclization was utilized for the stereoselective synthe
Modified tripeptides
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, (2008/06/13)
Modified oxytocin-vasopressin di- or tri-peptides wherein an amide group is replaced by a group selected from STR1 --CH2 NH--, --CH2 O--, --CH2 S--, --CH2 SO--, --CH2 SO2 --, --CH2/su
