79649-68-6Relevant academic research and scientific papers
A Copper-Catalyzed Aerobic [1,3]-Nitrogen Shift through Nitrogen-Radical 4-exo-trig Cyclization
Li, Yan,Wang, Rui,Wang, Tao,Cheng, Xiu-Fen,Zhou, Xin,Fei, Fan,Wang, Xi-Sheng
supporting information, p. 15436 - 15440 (2017/11/01)
A novel radical [1,3]-nitrogen shift catalyzed by copper diacetate under an oxygen atmosphere (1 atm) has been developed for the construction of a diverse range of indole derivatives from α,α-disubstituted benzylamine. In this reaction, oxygen was used as a clean terminal oxidant, and water was produced as the only by-product. Five inert bonds were cleaved, and two C?N bonds and one C?C double bond were constructed in one pot during this transformation. This unique method demonstrated broad application protential for the late-stage modification of biologically active natural products and drugs. Mechanistic investigations indicate that a unique 4-exo-trig cyclization of an aminyl radical onto a phenyl ring is involved in the catalytic cycle.
C-S bond cleavage in aromatic sulfide radical cations
Lanzalunga, Osvaldo
, p. 322 - 330 (2013/07/25)
The results of our recent studies of the structural effects on the C-S bond fragmentation process of aromatic sulfur radical cations are reported.
Dynamic path bifurcation in the Beckmann reaction: Support from kinetic analyses
Yamamoto, Yutaro,Hasegawa, Hiroto,Yamataka, Hiroshi
experimental part, p. 4652 - 4660 (2011/07/29)
The reactions of oximes to amides, known as the Beckmann rearrangement, may undergo fragmentation to form carbocations + nitriles when the migrating groups have reasonable stability as cations. The reactions of oxime sulfonates of 1-substituted-phenyl-2-propanone derivatives (7-X) and related substrates (8-X, 9a-X) in aqueous CH3CN gave both rearrangement products (amides) and fragmentation products (alcohols), the ratio of which depends on the system; the reactions of 7-X gave amides predominantly, whereas 9a-X yielded alcohols as the major product. The logk-logk plots between the systems gave excellent linear correlations with slopes of near unity. The results support the occurrence of path bifurcation after the rate-determining TS of the Beckmann rearrangement/fragmentation reaction, which has previously been proposed on the basis of molecular dynamics simulations. It was concluded that path-bifurcation phenomenon could be more common than thought and that a reactivity-selectivity argument based on the traditional TS theory may not always be applicable even to a well-known textbook organic reaction.
NOVEL BENZAMIDE DERIVATIVES AS MODULATORS OF THE FOLLICLE STIMULATING HORMONE
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Page/Page column 114, (2008/12/04)
The present invention provides new compounds of formula I, wherein Q, R1, R2, R4, R5, R6, Xi, R7, R8, M and G1 nare defined as in formula I; invention compounds are modulators of follicle-stimulating hormone - ("FSH") which are useful for male and female contraception as well as other disorders modulated by FSH receptor.
Catalytic oxidation of C-H bonds
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Page 7 - 8, (2008/06/13)
The invention provides a catalytic, chemospecific and stereospecific method of oxidizing a wide variety of substrates without unwanted side reactions. Essentially, the method of the instant invention, under relatively mild reaction conditions, catalytically, stereospecifically and chemospecifically inserts oxygen into a hydrocarbon C—H bond. Oxidation (oxygen insertion) at a tertiary C—H bond to form an alcohol (and in some cases a hemiacetal) at the tertiary carbon is favored. The stereochemistry of an oxidized tertiary carbon is preserved. Ketones are formed by oxidizing a secondary C—H bond and ring-cleaved diones are formed by oxidizing cis tertiary CH bonds.
Studies on development of sufficiently chemoselective N-acylation reagents: N-Acyl-N-(2,3,4,5,6-pentafluorophenyl)methanesulfonamides
Kondo, Kazuhiro,Sekimoto, Erika,Nakao, Junko,Murakami, Yasuoki
, p. 5843 - 5856 (2007/10/03)
A variety of storable N-acyl-N-(2,3,4,5,6-pentafluorophenyl)methanesulfonamides (4a-e) prepared from N-2,3,4,5,6-pentafluorophenylmethanesulfonamide (3), have been developed after systematic research on the structure-reactivity relationship and were found to serve as N-acylation reagents exhibiting sufficiently good chemoselectivity. (C) 2000 Elsevier Science Ltd.
Photoinduced electron transfer reactions of benzyl phenyl sulfides promoted by 9,10-dicyanoanthracene
Baciocchi, Enrico,Crescenzi, Cristina,Lanzalunga, Osvaldo
, p. 4469 - 4478 (2007/10/03)
The photoinduced oxidation of benzyl phenyl sulfides 1-3 has been investigated in MeCN using 9,10-dicyanoanthracene as sensitizer in the presence of O2. In this reaction a sulfide radical cation is formed, which undergoes one or more of the three main reaction pathways opened to these species: C-S bond cleavage, C-H bond cleavage and S-oxidation. The former route (leading to benzylic products) was observed with all the substrates investigated, whereas the second (leading to benzaldehydes) operates only with 1 and 2. Formation of sulfoxides was found solely in the photooxidation of 1. The influence of substrate structures on the relative contribution of the three pathways as well as the role of O2- in this respect are discussed.
The ortho-substituted N,N-diacetylaniline as a selective acetylating reagent
Murakami, Yasuoki,Kondo, Kazuhiro,Miki, Kazuki,Akiyama, Yoko,Watanabe, Toshiko,Yokoyama, Yuusaku
, p. 3751 - 3754 (2007/10/03)
Selective acetylation of the less hindered amino group in the presence of the more hindered amino group with the use of 2-trifluoromethyl-N,N-diacetylaniline 2c is described. This acetylation with 2c yielded the corresponding less hindered monoacetamide exclusively, simply, conveniently, and in good yields.
4-amino(alkyl)cyclohexane-1-carboxamide compound and use thereof
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, (2008/06/13)
4-Amino(alkyl)cyclohexane-1-carboxamide compounds of the formula (I) STR1 wherein each symbol is as defined in the Specification, isomers thereof and pharmaceutically acceptable acid addition salts thereof. The 4-amino(alkyl)cyclohexane-1-carboxamide comp
Amidomercuriation: A General Addition of Amides and Related Compounds to Olefins
Barluenga, Jose,Jimenez, Carmen,Najera, Carmen,Yus, Miguel
, p. 591 - 593 (2007/10/02)
The addition of different carboxamides and related compounds such as urethane or urea to olefins using mercury(II) nitrate followed by sodium borohydride reduction to give the corresponding N-substituted amides, urethanes, or ureas, respectively, is described.The monoalkylated ureas, through the same amidomercuriation-demercuriation procedure, yield symmetrical and unsymmetrical N,N'-disubstituted ureas.This amidomercuriation-demercuriation process provides a new, convenient, and general method for the Markovnikov amidation of carbon-carbon double bonds.
