2050-51-3Relevant articles and documents
Iron-Catalyzed Anti-Markovnikov Hydroamination and Hydroamidation of Allylic Alcohols
Ma, Wei,Zhang, Xiaohui,Fan, Juan,Liu, Yuxuan,Tang, Weijun,Xue, Dong,Li, Chaoqun,Xiao, Jianliang,Wang, Chao
supporting information, p. 13506 - 13515 (2019/09/09)
Hydroamination allows for the direct access to synthetically important amines. Controlling the selectivity of the reaction with efficient, widely applicable, and economic catalysts remains challenging, however. This paper reports an iron-catalyzed formal anti-Markovnikov hydroamination and hydroamidation of allylic alcohols, which yields γ-amino and γ-amido alcohols, respectively. Homoallylic alcohol is also feasible. The catalytic system, consisting of a pincer Fe-PNP complex (1-4 mol %), a weak base, and a nonpolar solvent, features exclusive anti-Markovnikov selectivity, broad substrate scope (>70 examples), and good functional group tolerance. The reaction could be performed at gram scale and applied to the synthesis of drug molecules and heterocyclic compounds. When chiral substrates are used, the stereochemistry and enantiomeric excess are retained. Further application of the chemistry is seen in the functionalization of amino acids, natural products, and existing drugs. Mechanistic studies suggest that the reaction proceeds via two cooperating catalytic cycles, with the iron complex catalyzing a dehydrogenation/hydrogenation process while the amine substrate acts as an organocatalyst for the Michael addition step.
Convergent synthesis of dronedarone, an antiarrhythmic agent
Okitsu, Takashi,Ogasahara, Mizuki,Wada, Akimori
, p. 1149 - 1153 (2016/08/11)
We have developed a convergent synthesis of dronedarone, an antiarrhythmic agent. The key steps of the process are the construction of a benzofuran skeleton by iodocyclization and the carbonylative Suzuki-Miyaura cross-coupling for biaryl ketone formation. This synthetic route required only eight steps from 2-amino-4-nitrophenol in 23% overall yield.
2'-(4,6-Disubstituted)-s-triazin-2-yl)amino-6'-dialkylamino flurans
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, (2008/06/13)
Fluorans useful as color precursors, particularly in the art of carbonless duplicating are normally colorless and are represented by the structural formula STR1 wherein R represents non-tertiary alkyl of one to four carbon atoms; R1 and R2 represent hydrogen or non-tertiary alkyl of one to four carbon atoms; R3 and R4 represent chlorine, NH2 or one of the groups --NR5 -(lower-alkylene)-N(R6)(R7), --NR5 -(lower-alkylene-N(R8)(R9)(R10) An, -NR5 -(lower-alkylene)-OH, -NR5 -(lower-alkylene) STR2 --NR5 -(HSO3 -C6 H4) or --O-(lower-alkylene)-N(R8)(R9) in which R5, R6 and R7 represent hydrogen or non-tertiary alkyl of one to four carbon atoms; R8 and R9 represent non-tertiary alkyl of one to four carbon atoms; R10 represents non-tertiary alkyl of one to four carbon atoms, benzyl or benzyl substituted in the benzene ring by one or two of halo or alkyl of one to three carbon atoms; and An represents an anion.
