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The 1,1-ADEQUATE spectrum clearly shows specific two-bond proton to carbon correlations to unequivocally distinguish the major and minor regioisomers of ortho-halogenated pyridines and to aid in assignment of the corresponding proton and carbon chemical shifts. M06-2X/6-31+G(d,p) free energies of the regioisomeric intermediates arising from deprotonation correctly predict the experimentally observed preference and thus can be used to tune the substituent pattern to yield a desired regiochemical outcome.

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Acceptor-donor compounds containing the isoquinoline N-oxide acceptor and (methoxy)nbenzene (n = 0, 1, 2, 3) electron donors were studied. The two chromophores are connected by a CH2 bridging unit. All acceptor-donor compounds exhibit photoinduced electron transfer in acid medium that results in the formation of a charge-transfer (CT) state. Measurements of the corresponding electronic emission spectra revealed that these bichromophoric systems exhibit a dual fluorescence that is strongly dependent on the protonation of the N-oxide function and the donor ability. The CT state responsible for the red-shifted luminescence in the studied compounds is directly connected with the initial excited state S1. On the basis of the spectroscopic and photochemical evidence, N – O bond scission is the dominant primary photochemical process involving the CT state, the subsequent radical coupling resulting in efficient aromatic hydroxylation. The outcome of both quenching and sensitization experiments confirms this assertion. The results strongly suggest that the ensuing photohydroxylation reaction is not a concerted process, but rather a two-step N – O bond scission followed by C – O bond formation, which is regioselectively guided by the electronic distribution of the resulting donor cation-radical.

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The invention belongs to the field of pharmaceutical chemistry, relates to a anti-tumor compounds 1 – alkenyl – isoquinoline derivatives preparation method and its application, the invention utilizes the isoquinoline nitrogen oxides in PdCl2 The catalysis of and olefin compounds coupling reaction to obtain the following structure. The present invention provides 1 – alkenyl – isoquinoline derivatives to various tumor cells exhibit excellent anti-tumor activity, can be used as a further development of the candidate or lead compound, is applied to the preparation of anti-cancer drug. (by machine translation)

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A vanadium-substituted polyoxometalate, K6[PW9V 3O40]·4H2O, was used as a recyclable and effective catalyst for the oxidation of pyridines. The reactions were successfully conducted in water under mild conditions. The catalyst could be easily recovered and reused.

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Deoxygenation of heteroaromatic N-oxides is commonly accomplished using chemical or enzymatic methods. In this work, we report on an expedient protocol for electrochemical reduction of pyridine N-oxide derivatives under mild conditions. A diverse range of mono- and bis N-oxides were converted into the corresponding nitrogen bases in good yields. Importantly, the method is highly selective towards N-oxides and tolerates challenging halo and nitro substituents in the heteroaromatic ring.

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A copper-mediated formally dehydrative biaryl coupling of azine N-oxides and oxazoles has been developed. The C-C bond-forming process proceeds, accompanied by the removal of the oxygen atom from the azine core, to directly afford the azine-oxazole biaryl linkage. Moreover, this system requires no noble transition metals such as palladium and rhodium, which are common promotors in the related dehydrogenative couplings with the azine N-oxide. Thus, the present protocol can provide a unique and less expensive approach to the azine-containing biheteroaryls of substantial interest in pharmaceutical and medicinal chemistry.

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The invention discloses a 2 – cyano quinoline derivative synthesis method, which belongs to the quinoline and its derivative synthesis method technical field, in formula (I) compounds and trimethyl cyanogen silane as raw materials, soluble in organic solvent, H – phosphorous acid diethyl ester in common under the catalysis of the carbon tetrachloride, alkali secondary acid agent, (II) compound […]; the invention provides 2 – cyano quinoline derivative synthesis method, the catalyst used in the cheap and easily obtained, the raw material is easy to store, mild reaction conditions, simple experimental operation, the product is easy to purify, high yield, is suitable for industrial production, for preparing 2 – cyano quinoline derivatives have provided a new synthesis method. (by machine translation)

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A highly efficient protocol for C-H/C-H cross-coupling has been found to occur between 2-aryl-1,2,3-triazole N-oxides and pyridine N-oxide derivatives. In addition, two homocoupling reactions of 2-substituted 1,2,3-triazole N-oxides and some pyridine N-oxide derivatives were developed. A possible pathway of C-H/C-H direct coupling is discussed.

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A dual C-H/N-H dehydrogenative coupling of quinoline-type N-oxides with sulfoximines that leads to N-(hetero)arylsulfoximines in high yields has been realized by using a catalytic amount of CuBr in air. The method does not require any additional ligand, base, reactivity modifier or oxidant and provides a practical route towards a series of sulfoximidoyl-functionalized quinolines and derivatives.

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A cascade reaction of isoquinoline N-oxides with alkynones was developed, delivering a fluorescent benzoazepino[2,1-a]isoquinoline derivative. The reaction worked smoothly without requirement of any catalyst or additive, making this method economical and easy to handle.

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