- A PASE-based approach towards 12-(1H-1,2,3-triazol-1-yl)-indolo[2,1-a]isoquinolines via the reaction of 3-(isoquinolin-1-yl)-1,2,4-triazines with benzyne
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12-(1H-1,2,3-Triazol-1-yl)indolo[2,1-a]isoquinolines are prepared in 51–56% yields using a PASE (pot, atom, step, economic)-based approach, namely, by the reaction between available 5-R-6-Ar-3-(isoquinolin-1-yl)-1,2,4-triazines and in situ generated benzyne. A mechanism comprising domino-transformation was suggested, and the structure of one key product was confirmed by a single crystal X-ray diffraction analysis.
- Gundala, Sravya,Guda, Mallikarjuna Reddy,Khasanov, Albert F.,Kopchuk, Dmitry S.,Krinochkin, Alexey P.,Santra, Sougata,Zyryanov, Grigory V.,Venkatapuram, Padmavathi,Garcia, Jarem Raul,Charushin, Valery N.
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Read Online
- Stereochemistry of c-4-bromo-r-1-cyano-t-3-methoxy-1,2,3,4- tetrahydroisoquinolines from isoquinoline Reissert compounds
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Treatment of 2-acyl (or sulfonyl)-1-cyano-1,2-dihydroisoquinolines with bromine and CH3OH gave 2-acyl (or sulfonyl)-4-bromo-1-cyano-3-methoxy- 1,2,3,4-tetrahydroisoquinolines in a highly stereoselective manner in high yields. The stereochemistry, with 1,4-cis and 3,4-trans configurations, was determined by X-ray crystallography.
- Sugiura, Michiharu,Asai, Koosuke,Hamada, Yoshiki,Hatano, Keiichiro,Kurono, Yukihisa,Suezawa, Hiroko,Hirota, Minoru
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Read Online
- Highly chemoselective deoxygenation of N-heterocyclic: N -oxides under transition metal-free conditions
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Because their site-selective C-H functionalizations are now considered one of the most useful tools for synthesizing various N-heterocyclic compounds, the highly chemoselective deoxygenation of densely functionalized N-heterocyclic N-oxides has received much attention from the synthetic chemistry community. Here, we provide a protocol for the highly chemoselective deoxygenation of various functionalized N-oxides under visible light-mediated photoredox conditions with Na2-eosin Y as an organophotocatalyst. Mechanistic studies imply that the excited state of the organophotocatalyst is reductively quenched by Hantzsch esters. This operationally simple technique tolerates a wide range of functional groups and allows high-yield, multigram-scale deoxygenation. This journal is
- Kim, Se Hyun,An, Ju Hyeon,Lee, Jun Hee
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supporting information
p. 3735 - 3742
(2021/05/04)
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- A convenient reagent for the conversion of aldoximes into nitriles and isonitriles
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For the dehydroxylation of aldoximes with 4-nitro-1-((trifluoromethyl)sulfonyl)-imidazole (NTSI), slight modifications of reaction conditions resulted in significantly different reaction paths to provide either nitriles or isonitriles. The challenging conversion of aldoximes into isonitriles was achieved under mild conditions.
- Zhang, Wei,Lin, Jin-Hong,Zhang, Pengfei,Xiao, Ji-Chang
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supporting information
p. 6221 - 6224
(2020/06/29)
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- Metal-free, redox-neutral, site-selective access to heteroarylamine via direct radical?radical cross-coupling powered by visible light photocatalysis
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Transition-metal-catalyzed C?N bond-forming reactions have emerged as fundamental and powerful tools to construct arylamines, a common structure found in drug agents, natural products, and fine chemicals. Reported herein is an alternative access to heteroarylamine via radical?radical cross-coupling pathway, powered by visible light catalysis without any aid of external oxidant and reductant. Only by visible light irradiation of a photocatalyst, such as a metal-free photocatalyst, does the cascade single-electron transfer event for amines and heteroaryl nitriles occur, demonstrated by steady-state and transient spectroscopic studies, resulting in an amine radical cation and aryl radical anion in situ for C?N bond formation. The metal-free and redox economic nature, high efficiency, and site-selectivity of C?N cross-coupling of a range of available amines, hydroxylamines, and hydrazines with heteroaryl nitriles make this protocol promising in both academic and industrial settings.
- Zhou, Chao,Lei, Tao,Wei, Xiang-Zhu,Ye, Chen,Liu, Zan,Chen, Bin,Tung, Chen-Ho,Wu, Li-Zhu
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supporting information
p. 16805 - 16813
(2020/11/09)
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- Synthesis method of 2-cyanoquinoline derivative
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The invention discloses a synthesis method of a 2-cyanoquinoline derivative, and belongs to the technical field of synthesis methods of chinoline and derivatives thereof. The synthesis method includes: adopting a compound represented as in formula (I) and trimethylsilyl cyanide as raw materials, dissolving the raw materials in an organic solvent, catalyzing with H-diethyl phosphite and carbon tetrachloride, and adopting alkali as a deacid reagent to prepare a compound represented as in formula (II). The synthesis method of the 2-cyanoquinoline derivative has the advantages that the adopted catalysts are low in cost and easy to obtain, the raw materials are easy to store, reaction conditions are mild, experimental operations are simple, the obtained 2-cyanoquinoline derivative products are easy to purify, high yield and applicability to industrial production are realized, and a novel synthesis method for preparing the 2-cyanoquinoline derivative is provided.
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Paragraph 0089-0093
(2019/10/04)
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- Regioselective Cyanation of Six-Membered N-Heteroaromatic Compounds Under Metal-, Activator-, Base- and Solvent-Free Conditions
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A regioselective cyanation of heteroaromatic N-oxides with trimethylsilyl cyanide has been developed to obtain 2-substituted N-heteroaromatic nitrile without the requirement of any external activator-, metal-, base-, and solvent. The present protocol is a straightforward, one-pot heteroaromatic C?H cyanation process, and proceeds smoothly in conventional heating but also under microwave irradiation with shorter reaction times. This approach now allows access to a broad class of quinoline N-oxides and other heteroarene N-oxides with high to good yields and can also be scaled up to obtain gram quantities. Further application of this process was observed and utilized in late-stage cyanation of the anti-malarial drug quinine as well as transformation of the 2-cyanoazines to a series of biologically important molecules. Based on the experimental observations, a plausible mechanism has also been proposed highlighting the dual role of trimethylsilyl cyanide as a nitrile source and as an activating agent. (Figure presented.).
- Sarmah, Bikash Kumar,Konwar, Monuranjan,Bhattacharyya, Dipanjan,Adhikari, Priyanka,Das, Animesh
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supporting information
p. 5616 - 5625
(2019/11/22)
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- Hypervalent Iodine(III)-Mediated Regioselective Cyanation of Quinoline N-Oxides with Trimethylsilyl Cyanide
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A regioselective cyanation of quinoline N-oxides with trimethylsilyl cyanide was developed by using (Diacetoxyiodo) benzene (PIDA) as mediated hypervalent iodine(III) reagent under metal-free and base-free reaction conditions to obtain 2-cyanoquinolines. The efficient PIDA reagent could play the role of an activator of the substrates and an accelerator of N?O bond cleavage. The reaction system featured a wide range of substrate suitability and high yields. The procedure was enlarged gram-scale to synthesize the tuberculosis (TB) inhibitor. Finally, according to some experimental results, a plausible mechanism for the cyanation reaction is proposed. (Figure presented.).
- Xu, Feng,Li, Yuqin,Huang, Xin,Fang, Xinjie,Li, Zhuofei,Jiang, Hongshuo,Qiao, Jingyi,Chu, Wenyi,Sun, Zhizhong
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supporting information
p. 520 - 525
(2018/12/13)
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- Preparation method of aromatic nitrile compound or heteroaromatic nitrile compound
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The invention discloses a preparation method of an aromatic nitrile compound or a heteroaromatic nitrile compound. The preparation method comprises: under the protection of an inert gas, in a solvent,under the actions of a nickel catalyst, a ligand, metal zinc and an additive, carrying out a reaction on a cyanation reagent and halogenated aromatic hydrocarbon or halogenated heteroaromatic hydrocarbon. According to the present invention, by using the inexpensive and easily-available nickel catalyst and the ligand, the halogenated aromatic hydrocarbon or halogenated heteroaromatic hydrocarbon,especially the chlorinated aromatic hydrocarbon or chlorinated heteroaromatic hydrocarbon with characteristics of low price, easy obtaining and low reaction activity can mildly and efficiently react with the cyanation reagent with low toxicity to prepare the aromatic nitrile compound or heteroaromatic nitrile compound; and the preparation method has advantages of simple operation, mildness, high efficiency and the like, and further has characteristics of good functional group compatibility, good universality of substrate and the like.
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Paragraph 0043; 0045; 0204-0206
(2018/11/03)
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- C?H Cyanation of 6-Ring N-Containing Heteroaromatics
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Heteroaromatic nitriles are important compounds in drug discovery, both for their prevalence in the clinic and due to the diverse range of transformations they can undergo. As such, efficient and reliable methods to access them have the potential for far-reaching impact across synthetic chemistry and the biomedical sciences. Herein, we report an approach to heteroaromatic C?H cyanation through triflic anhydride activation, nucleophilic addition of cyanide, followed by elimination of trifluoromethanesulfinate to regenerate the cyanated heteroaromatic ring. This one-pot protocol is simple to perform, is applicable to a broad range of decorated 6-ring N-containing heterocycles, and has been shown to be suitable for late-stage functionalization of complex drug-like architectures.
- Elbert, Bryony L.,Farley, Alistair J. M.,Gorman, Timothy W.,Johnson, Tarn C.,Genicot, Christophe,Lallemand, Bénédicte,Pasau, Patrick,Flasz, Jakub,Castro, José L.,MacCoss, Malcolm,Paton, Robert S.,Schofield, Christopher J.,Smith, Martin D.,Willis, Michael C.,Dixon, Darren J.
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supporting information
p. 14733 - 14737
(2017/10/07)
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- A Bifunctional Reagent Designed for the Mild, Nucleophilic Functionalization of Pyridines
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Herein is reported the design and application of a reagent for the direct functionalization of pyridines. These reactions occur under mild conditions and exhibit broad functional group tolerance, enabling the late-stage functionalization of drug-like molecules. The reagent can be easily prepared on large scale from inexpensive reagents, and reacts in the title reaction with acetonitrile, sodium chloride, and sodium methanesulfonate as the sole byproducts. Although this Communication focuses primarily on reactions with cyanide as nucleophile, preliminary experiments with other nucleophiles foreshadow the broad reaching synthetic utility of this approach.
- Fier, Patrick S.
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supporting information
p. 9499 - 9502
(2017/07/24)
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- General and Mild Nickel-Catalyzed Cyanation of Aryl/Heteroaryl Chlorides with Zn(CN)2: Key Roles of DMAP
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A new and general nickel-catalyzed cyanation of hetero(aryl) chlorides using less toxic Zn(CN)2 as the cyanide source has been developed. The reaction relies on the use of inexpensive NiCl2·6H2O/dppf/Zn as the catalytic system and DMAP as the additive, allowing the cyanation to occur under mild reaction conditions (50-80 °C) with wide functional group tolerance. DMAP was found to be crucial for successful transformation, and the reaction likely proceeds via a Ni(0)/Ni(II) catalysis based on mechanistic studies. The method was also successfully extended to aryl bromides and aryl iodides.
- Zhang, Xingjie,Xia, Aiyou,Chen, Haoyi,Liu, Yuanhong
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supporting information
p. 2118 - 2121
(2017/04/27)
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- Reactions of ethyl cyanoformate with cycloimmonium salts: a direct pathway to fused or substituted azaheterocycles
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Aromatic cycloimmonium salts underwent different reaction pathways when treated with ethyl cyanoformate in triethyl amine medium, including selective γ-cyano substitutions (in case of phenanthrolinium and quinolinium salts) and 3+2 dipolar cycloadditions (for phthalazinium and isoquinolinium salts). When using phthalazinium salts, besides the 3+2 cycloaddition products (imidazo[2,1-a]phthalazines), we obtained 8,8a,16,16a-tetrahydropyrazino-[2,1-a;4,5-a′]-diphthalazines as secondary products via a 3+3 cycloaddition dimerization. The structures of the synthesized compounds have been proved by spectral data, and X-ray diffraction for three of the new derivatives.
- Al Matarneh, Cristina M.,Apostu, Mircea O.,Mangalagiu, Ionel I.,Danac, Ramona
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p. 4230 - 4238
(2016/07/06)
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- Iodine-catalyzed ammoxidation of methyl arenes
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The development of organic transformation using cheap and readily available substrates under mild conditions will be pivotal for green and sustainable synthetic organic chemistry. Concerning our continued interest in the cyanation reaction, a metal-free direct ammoxidation of readily available methyl arenes leading to nitriles was established under mild conditions. A series of aryl methanes especially heteroaryl methanes (30 examples) were applicable in moderate to good yields with good functionality tolerance.
- Guo, Songjin,Wan, Gen,Sun, Song,Jiang, Yan,Yu, Jin-Tao,Cheng, Jiang
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supporting information
p. 5085 - 5088
(2015/03/30)
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- Copper(II) acetate mediated conversion of ortho aminomethyl substituted isoquinolines to bis(isoquinolylcarbonyl)amides
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An ethanolic solution of ortho aminomethyl substituted isoquinolines, on stirring in air with half equivalent of [Cu(OAc)2(H2O)], afforded [Cu(1-L)(OAc)] (1) and [Cu(3-L)(OAc)] (2) {1-L = bis(1- isoquinolylcarbonyl)amide ion and 3-L = bis(3-isoquinolylcarbonyl)amide ion}. This reaction involves the oxidation of a methylene group and the formation of a bond between nitrogen and carbon in N-C(O) through coupling. The free ligands can be isolated as crystalline solids from compounds 1-2, by extrusion of the Cu2+ ion using EDTA2-. The molecular structure of 1·2.5H2O has been established and the copper(II) center has a pseudo square-planar N3O environment. A packing diagram shows the existence of a centrosymmetric dimer in which two copper centers are intermolecularly linked by the O2 atom of the amide function, leading to a Cu2O2 unit.
- Sahu, Rojalin,Fulwa, Vijendra Kumar,Jena, Himanshu Sekhar,Manivannan, Vadivelu
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scheme or table
p. 9 - 12
(2012/03/09)
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- PTERIDINONES AS INHIBITORS OF POLO - LIKE KINASE
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The present invention provides compounds having a structure according to Formula (I) or a salt or solvate thereof, wherein ring A, X, R1, R2, R3, R4, R5 and R6, are defined herein. The invention further provides pharmaceutical compositions including the compounds of the invention and methods of making and using the compounds and compositions of the invention, e.g., in the treatment and prevention of various disorders, such as Parkinson's disease.
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Page/Page column 108; 109
(2011/07/09)
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- Synthesis of quinolinyl and isoquinolinyl phenyl ketones as novel agonists for the cannabinoid CB2 receptor
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A series of quinolinyl and isoquinolinyl phenyl ketones was synthesized and their CB2 receptor-dependent G-protein activities were determined using the [35S]GTPγS binding assay. Both quinoline and isoquinoline derivatives exhibited similar CB2 receptor agonist activity, the most potent ligands being the 2-(Me2N)-phenyl substituted derivatives, which were also full agonists at the CB2-receptor.
- Reux, Bastien,Nevalainen, Tapio,Raitio, Katri H.,Koskinen, Ari M.P.
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experimental part
p. 4441 - 4447
(2009/11/30)
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- Iodine-mediated electrophilic cyclization of 2-alkynylbenzaldoximes leading to the formation of iodoisoquinoline N-oxides
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Reaction of 2-alkynylbenzaldoximes 1 with 5 equiv of iodine in EtOH at room temperature gives the corresponding iodoisoquinoline N-oxides 2 in good to excellent yields. The cyclization proceeds very smoothly and quickly without any additives such as bases
- Huo, Zhibao,Tomeba, Hisamitsu,Yamamoto, Yoshinori
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p. 5531 - 5533
(2008/12/22)
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- Protoberberines from Reissert-Compounds VIII [1]. Oxazoloisoquinolines, New and Efficient Educts for the Synthesis of 8-Oxoprotoberberines
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Certain benzylated oxazoloisoquinolinones readily available from Reissert compounds provided an efficient access to 8-oxoprotoberberines in three steps. A series of these new precursors as well as several oxoprotoberberines were prepared and the scope and limitation of this procedure were investigated.
- Reimann, Eberhard,Grasberger, Fritz,Polborn, Kurt
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p. 991 - 1014
(2007/10/03)
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- The Nucleophilicity of Superoxide towards Different Alkyl Halides Estimated from Kinetic Measurements
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Values of the rate constant ksub are measured for the substitution reaction between superoxide O2 anion-radical and the alkyl halides butyl chloride, 2-butyl chloride, benzyl chloride, ethyl bromide, butyl bromide, 2-butyl bromide, neopentyl bromide, benzyl bromide, (1-bromo-2,2-dimethylpropyl)benzene and 1-iodoadamantane.These rate constants are compared with the expected rate constant kET for the electron transfer reaction between the same alkyl halides and an aromatic anion radical A anion-radical with the same standard oxidation potential as O2 anion-radical.The ksub/kET ratios show that the mechanism of the substitution reaction amy shift from SN2-like to ET-like on changes in the steric hindrance and the acceptor ability of the alkyl halide.The influence on ksub/kET of the difference in self-exchange reorganization energy λ(0) between O2 anion-radical/O2 and A anion-radical/A is discussed.
- Daasbjerg, Kim,Lund, Henning
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p. 597 - 604
(2007/10/02)
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- Synthesis and nucleophilic reactions of cyano substituted N-methoxyisoquinolinium salts
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Starting from isoquinoline, the cyano substituted N-methoxyisoquinolinium salts 1.1 and 1.4 are prepared. Their behaviour in the presence of O-, C- and N-nucleophiles in different aprotic solvents is examined: from the 1-cyano substituted isoquinolinium derivative 1.1, 1- and 3-aminals or 1-iminium salts are obtained depending on the amine used, and N-methoxyisocarbostyril 4.1.1 in H2O and OH-. The reaction of the 4-cyano-N-methoxyisoquinolinium salt 1.4 with amines yields 1-aminals and with OH- the corresponding hemiaminal. Conversion with CN- results in dinitrile derivatives and N-oxides.
- Heber,Holzgrabe,Werra
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p. 785 - 790
(2007/10/02)
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- Reissert Compound Studies. LXV. Praparation of Reissert Compounds Derived from α,β-Unsaturated Acid Chlorides
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Reissert compounds derived from α,β-unsaturated acid chlorides were prepared.The conjugate base obtained from these Reissert compounds exhibited the following carbanion reactions: 1) Alkylation, 2) Condensation with benzaldehyde, 3) Rearrangement to give dimeric compounds rather than simple rearranged compounds.In the case of alkylated isoquinoline Reissert compounds, the attempted rearrangement led to ring annellated amines.
- Hahn, Jung-Tai,Kant, Joydeep,Popp, Frank D.,Chhabra, Siri Ram,Uff, Barrie C.
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p. 1165 - 1176
(2007/10/02)
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- PREPARATION OF HETEROARENECARBONITRILES BY REACTION OF HETEROARENE N-OXIDES WITH TRIMETHYLSILYL CYANIDE IN THE PRESENCE OF DBU
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Several heteroarenecarbonitriles were prepared from the corresponding heteroarene N-oxides by treatment with trimethylsilylcyanide (TMSCN) in the presence of a base in tetrahydrofuran (THF). 1,8-Diazabicyclo-7-undecene (DBU) was found to be an effective base for the cyanation.
- Miyashita, Akira,Kawashima, Touru,Iijima, Chihoko,Higashino, Takeo
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p. 211 - 218
(2007/10/02)
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- Sels de N-Alcoxyquinoleinium et de N-Alcoxyisoquinoleinium Porteurs d'une Fonction Ester dans leur Chaine Alcoxyle: Synthese et Reactivite vis-a-vis des Ions Cyanure
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Reaction of ethyl α-bromoisobutyrate on quinoline 1 oxide and isoquinoline 2-oxide in the presence of silver perchlorate leads to the corresponding N-alkoxyl salts 1 and 2.On treatment with potassium cyanide, these salts are converted into 2-cyanoquinoline and 1-cyanoisoquinoline according to mode B of the Katritzky's classification concerning the reaction of nucleophiles on N-alkoxypyridinium salts.When the reaction of canide ions were performed on salt 1 at 0 deg C in aqueous solution the dihydro aromatic adduct 4 was isolated.This result confirms the addition-elimination mechanism of the reaction studied.
- Sliwa, Henri,Randria-Raharimanana, Clarisse,Ouattara, Lassina
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p. 627 - 630
(2007/10/02)
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- Tetrahydrofolate Coenzyme Models: Synthesis of Tetrahydroimidazoisoquinolines and Tetrahydroimidazoquinolines
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The new dihydroimidazoles 3-methyl-1,5,6,10b-tetrahydroimidazoisoquinoline and 1-methyl-3,3a,4,5-tetrahydroimidazoquinoline are efficiently and conveniently prepared from isoquinoline and quinoline, via 1-aminomethyl-1,2,3,4-tetrahydroisoquinoline and 2-aminomethyl-1,2,3,4-tetrahydroquinoline, respectively.Deprotonation of the fused dihydroimidazoles at the methyl substituent leads to homologation via C-alkylation, C-acylation, or C-phosphonylation-condensation.The properties of the tetrahydroimidazoisoquinolines and tetrahydroimidazoquinolines towards reducing agents mirror those of monocyclic dihydroimidazoles, affording aminomethyl-isoquinolines and -quinolines, respectively.
- Jones, Raymond C. F.,Smallridge, Mark J.,Chapleo, Christopher B.
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p. 385 - 391
(2007/10/02)
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- Some Reactions of N-Alkoxycarbonyl Reissert Compounds with Heterocumulenes: Formation of the Imidazoisoquinoline and Imidazophthalazine Systems and Related Chemistry
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Chloroformate derived Reissert compounds of isoquinoline and of phenanthridine on treatment with base undergo cyclisation with isothiocyanates to give in good yields corresponding imidazoisoquinoline and imidazophenanthroline derivatives.Phthalazine Reissert compound analogues give open chain adducts under the same conditions which can be cyclised to derivatives of the novel imidazophthalazine system by heating in the presence of molecular sieves.When carbon disulphide is the heterocumulene cyclisation is not observed but open chain dithio-ester derivatives can be isolated on alkylation of the intermediate sodium salts.
- Uff, Barrie C.,Budhram, Ronald S.,Ghaem-Maghami, Ghobad,Mallard, Angela S.,Harutunian, Vahak,et al.
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p. 1901 - 1930
(2007/10/02)
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- THE SYNTHESIS OF (+)- AND (-)-1-(1-ISOQUINOLINYL)-1-(2-PYRIDYL)ETHANOL. A CHIRAL LIGAND WITH USEFUL CHELATING PROPERTIES.
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(+/-)-1-(1-isoquinolinyl)-1-(2-pyridyl)ethanol has been prepared and the two enantiomers have been resolved by derivatization with a chiral isocyanate followed by a chromatographic separation.The relative configurations of the diastereomers are discussed in relation to their chromatographic behaviour and NMR spectral data.The enantiomeric alcohols obtained after hydrolysis of the diastereomeric carbamates can be alkylated or attached to a Merrifield resin to afford useful chiral chelating ligands for transition metals.
- Elman, Bjoern,Moberg, Christina
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p. 223 - 228
(2007/10/02)
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- Synthetic Applications of N-N Linked Heterocycles. Part 10. Preparation of Novel N-N Linked Biheteroaryl Monocations, their Reactions with Nucleophiles, and Electrophilic Reactions of some Dihydro-derivatives
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Novel N-N linked biheteroaryl monocations are prepared from N-aminopyridinium, -quinolinium, or -isoquinolinium salts, with dehydroacetic acid, cyclic anhydrides, hexane-2,4-dione, or the benzoxazinone (15).Reactions of dihydro-derivatives (from reduction of the cations with sodium borohydride or sodium dithionite) with electrophiles are investigated.Reactivity towards nucleophiles was studied to evaluate, (a) the regioselectivity of nucleophilic addition, and (b) the ease of decomposition of the resulting adducts into 4-substituted pyridines.
- Katritzky, Alan R.,Ibrahim, M. Hussain,Valnot, Jean-Yves,Sammes, Michael P.
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p. 859 - 881
(2007/10/02)
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- NEW METHODS AND REAGENTS IN ORGANIC SYNTHESIS. 12. REACTION OF DIETHYL PHOSPHOROCYANIDATE (DEPC) WITH AROMATIC AMINE OXIDES. A MODIFIED REISSERT-HENZE REACTION
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Diethyl phosphorocyanidate (DEPC) reacts with aromatic amine oxides in the presence of triethylamine to give α-cyanated compounds; the reaction may be called a modified Reissert-Henze reaction.
- Harusawa, Shinya,Hamada, Yasumasa,Shioiri, Takayuki
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p. 981 - 984
(2007/10/02)
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- Reissert Compound Studies. XLII. Synthesis and Reactions of the 3,4-Dihydro-β-carboline Reissert Compound and Observations on α, β, and γ-Carbolines
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3,4-Dihydro-β-carboline and benzo-γ-carboline yielded Reissert compounds.The 3,4-dihydro-β-carboline Reissert compound, through its acid- and base-promoted reactions, was found to be a very useful intermediate in the synthesis of several β-carboline de
- Veeraraghavan, Seshardi,Popp, Frank D.
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p. 909 - 915
(2007/10/02)
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- Air oxidation of Reissert compounds
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Reissert compounds undergo autoxidation in basic solution giving rise to isoquinaldo- or quinaldonitriles.Under the same reaction conditions, dihydroisoquinoline Reissert compounds undergo oxidative decyanation to dihydroisocarbostirils.The intermediacy of α-peroxycyanides is proposed in this transformation.
- Rozwadowska, Maria,Brozda, Danuta
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p. 1239 - 1242
(2007/10/02)
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