33149-71-2Relevant academic research and scientific papers
Selective Synthesis of Primary Anilines from NH3 and Cyclohexanones by Utilizing Preferential Adsorption of Styrene on the Pd Nanoparticle Surface
Koizumi, Yu,Jin, Xiongjie,Yatabe, Takafumi,Miyazaki, Ray,Hasegawa, Jun-ya,Nozaki, Kyoko,Mizuno, Noritaka,Yamaguchi, Kazuya
supporting information, p. 10893 - 10897 (2019/07/12)
Dehydrogenative aromatization is one of the attractive alternative methods for directly synthesizing primary anilines from NH3 and cyclohexanones. However, the selective synthesis of primary anilines is quite difficult because the desired primary aniline products and the cyclohexanone substrates readily undergo condensation affording the corresponding imines (i.e., N-cyclohexylidene-anilines), followed by hydrogenation to produce N-cyclohexylanilines as the major products. In this study, primary anilines were selectively synthesized in the presence of supported Pd nanoparticle catalysts (e.g., Pd/HAP, HAP=hydroxyapatite, Ca10(PO4)6(OH)2) by utilizing competitive adsorption unique to heterogeneous catalysis; in other words, when styrene was used as a hydrogen acceptor, which preferentially adsorbs on the Pd nanoparticle surface in the presence of N-cyclohexylidene-anilines, various structurally diverse primary anilines were selectively synthesized from readily accessible NH3 and cyclohexanones. The Pd/HAP catalyst was reused several times though its catalytic performance gradually declined.
Pd-tBuONO Cocatalyzed Aerobic Indole Synthesis
Ning, Xiao-Shan,Liang, Xin,Hu, Kang-Fei,Yao, Chuan-Zhi,Qu, Jian-Ping,Kang, Yan-Biao
supporting information, p. 1590 - 1594 (2018/04/30)
A Pd-tBuONO co-catalyzed scalable and practical synthesis of indoles with molecular oxygen as terminal oxidant is developed. Either terminal or internal 2-vinylanilines could be smoothly converted to desired indoles under one general condition. This method has been evaluated in the large scale synthesis of indomethacin and a potential anti-breast cancer drug candidate 1. (Figure presented.).
Selenium-catalyzed oxidative c(sp2)-h amination of alkenes exemplified in the expedient synthesis of (Aza-)indoles
Ortgies, Stefan,Breder, Alexander
supporting information, p. 2748 - 2751 (2015/06/16)
A new selenium-catalyzed protocol for the direct, intramolecular amination of C(sp2)-H bonds using N-fluorobenzenesulfonimide as the terminal oxidant is reported. This method enables the facile formation of a broad range of diversely functionalized indoles and azaindoles derived from easily accessible ortho-vinyl anilines and vinylated aminopyridines, respectively. The procedure exploits the pronounced carbophilicity of selenium electrophiles for the catalytic activation of alkenes and leads to the formation of C(sp2)-N bonds in high yields and with excellent functional group tolerance.
Highly Diastereo- and Enantioselective CuH-Catalyzed Synthesis of 2,3-Disubstituted Indolines
Ascic, Erhad,Buchwald, Stephen L.
supporting information, p. 4666 - 4669 (2015/04/27)
A diastereo- and enantioselective CuHcatalyzed method for the preparation of highly functionalized indolines is reported. The mild reaction conditions and high degree of functional group compatibility as demonstrated with substrates bearing heterocycles,
A new entry to the phenanthridine ring system
Mondal, Poulomi,Thander, Latibuddin,Chattopadhyay, Shital K.
supporting information; scheme or table, p. 1328 - 1331 (2012/04/04)
A new synthesis of phenanthridine derivatives having three-point diversity has been developed based on the sequential application of three-atom economic processes viz. aza-Claisen rearrangement, ring-closing enyne metathesis and Diels-Alder reaction as key steps. An unexpected isomerisation was observed during aza-Claisen rearrangement of N-allylanilines which may open up new opportunities in heterocyclic synthesis.
Pd-catalyzed arylation/ring-closing metathesis approach to azabicycles
Martínez-Estíbalez, Unai,Sotomayor, Nuria,Lete, Esther
, p. 2919 - 2922 (2008/02/03)
Palladium-catalyzed arylation followed by Grignard addition to imines and ring-closing metathesis, using Grubbs' catalysts, provides a route to six-, seven-, and eight-membered azabicycles.
New pathway to the synthesis of substituted 4H-3,1-benzoxazines
Mochalov,Gazzaeva,Fedotov,Shabarov,Zefirov
, p. 794 - 801 (2007/10/03)
The intramolecular rearrangement of N-acyl-2-cyclopropylanilines by the action of protic acids gives substituted 4H-3,1-benzoxazines. The reaction proceeds in high yield through the formation of benzoxazine precursors, namely, the corresponding 3,1-benzoxazinium ions, which are stable in acid solution. N-Acylamino-2-alkenylbenzenes, in which the double bond of the alkyl chain is conjugated with the benzene ring, are capable of undergoing a similar rearrangement.
Pyrolyses of o-Alkoxy- and o-Alkylthio-N-Allylanilines and of Some Related O- and S-Allyl Compounds
Cadogan, J. I. G.,Hickson, Clare L.,McNab, Hamish
, p. 1885 - 1890 (2007/10/02)
The o-substituted allyl compounds (1)-(12) have been pyrolysed in order to generate aminyl, phenoxyl, and thiophenoxyl radicals with adjacent substituents.In all cases, products are formed by intramolecular hydrogen transfer from the substituent to the radical centre.This process may be followed by rearrangement to give an aldehyde, by heteroatom extrusion to give an alkene, or by ring formation to give five-membered ring heterocycles (Scheme 1, routes A, B1, and B2 respectively.The distribution of products formed by each route is dependent both on the nature of the o-substituent, and on the nature of the initial radical.
Fluxionality in (cyclohtptatriene)iron tricarbonyl complexes
Karel, Karin J.
, p. 419 - 430 (2008/10/08)
1H NMR spin saturation transfer experiments were undertaken to measure the barrier for 1,3 iron shifts in (cyclobeptatriene)iron tricarbonyl (CHT = cycloheptatriene) complexes.
Intramolecular 1,1-Cycloaddition of Nitrilimines as a Route to Benzodiazepines and Cyclopropacinnolines
Padwa, Albert,Nahm, Steven
, p. 1402 - 1409 (2007/10/02)
Treatment of o-vinylphenyl-substituted chloroglyoxylate phenylhydrazones with base leads to nitrilimines.These reactive 1,3-dipoles undergo intramolecular 1,1-cycloaddition with complete retention of configuration to give cyclopropacinnolines.When the
