- Synthesis of Isoquinolines from Indenes
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A general procedure for the synthesis of isoquinolines from appropriately substituted indenes is described.Ozonolysis of the indenes followed by reductive workup gives intermediate homophthalaldehydes which are treated with ammonium hydroxide to give the isoquinolines.This "one-pot", three-step reaction sequence was applied to the formation of all of the mono-C-methyl-substituted isoquinolines in a regiospecific manner.The procedure is applicable to both electron-withdrawing and electron-donating substituents on the indene system.In this manner the 6- and 7-nitro-,-bromo-, and -iodoisoquinolines were prepared.
- Miller, R. Bryan,Frincke, James M.
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- Palladium-Catalyzed Isoquinoline Synthesis by Tandem C-H Allylation and Oxidative Cyclization of Benzylamines with Allyl Acetate
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A novel approach to synthesize 3-methylisoquinolines via a one-pot, two-step, palladium(II)-catalyzed tandem C-H allylation/intermolecular amination and aromatization is reported. A wide series of 3-methylisoquinoline derivatives were obtained directly using this method in moderate to good yields, and we highlight the synthetic importance of this new transformation.
- Chen, Yujie,Huang, Zhibin,Dai, Chenyang,Yang, Shan,Shi, Da-Qing,Zhao, Yingsheng
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- Cu(II)-Catalyzed Construction of Heterobiaryls using 1-Diazonaphthoquinones: A General Strategy for the Synthesis of QUINOX and Related P,N Ligands
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An efficient and straightforward method was developed for the synthesis of heterobiaryls using easily available N-oxides and diazonaphthoquinones under cheap Cu(II) catalysis. The developed method offered QUINOX and related congeners in a simple manner. A wide scope of important heterobiaryls was achieved with high site selectivity. The synthesized naphthols were transformed into the privileged related P,N ligands. Suitable resolution methods can directly afford the corresponding axially chiral heterobiaryls.
- Biswas, Aniruddha,Pan, Subarna,Samanta, Rajarshi
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supporting information
p. 1631 - 1636
(2022/03/14)
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- Preparation method of isoquinoline compound
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The invention discloses a preparation method of isoquinoline compounds, benzylamine protected by oxamide and allyl acetate are used as raw materials, a series of isoquinoline compounds are obtained through a cascade reaction of C-H bond functionalization and hydrolysis and two-step one-pot synthesis, and the used raw materials are simple and easy to obtain, reaction conditions are mild, and post-treatment is simple.
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Paragraph 0022-0023
(2021/03/07)
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- Potassium tert-Butoxide-Promoted Acceptorless Dehydrogenation of N-Heterocycles
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Potassium tert-butoxide-promoted acceptorless dehydrogenation of N-heterocycles was efficiently realized for the generation of N-heteroarenes and hydrogen gas under transition-metal-free conditions. In the presence of KOtBu base, a variety of six- and five-membered N-heterocyclic compounds efficiently underwent acceptorless dehydrogenation to afford the corresponding N-heteroarenes and H2 gas in o-xylene at 140 °C. The present protocol provides a convenient route to aromatic nitrogen-containing compounds and H2 gas. (Figure presented.).
- Liu, Tingting,Wu, Kaikai,Wang, Liandi,Yu, Zhengkun
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supporting information
p. 3958 - 3964
(2019/08/01)
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- Synthesis of Arylamines via Non-Aerobic Dehydrogenation Using a Palladium/Carbon-Ethylene System
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The reaction of cyclohexanones with amines proceeded under an ethylene atmosphere in the presence of a catalytic amount of palladium/carbon to afford a variety of arylamines in good to high yields. The present reaction was carried out under completely non-aerobic conditions, and which is in contrast with the previously reported aerobic system. has wide applicability affording a variety of aromatic amines, and co-product of the reaction is only gaseous ethane. Thus, this method is environmentally friendly. This protocol was applied intramolecularly to provide a novel method for the construction of quinoline and isoquinoline compounds. (Figure presented.).
- Shimomoto, Yuya,Matsubara, Ryosuke,Hayashi, Masahiko
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p. 3297 - 3305
(2018/08/07)
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- Asymmetric synthesis of a TRPV1 antagonist via tert -butanesulfinamide- directed reductive amination with a chromanone
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An expedient asymmetric synthesis of TRPV1 antagonist 1 has been developed and demonstrated on multikilogram scale. The enabling route to 1 is detailed herein and characterized by the following key transformations: an aldol-cyclodehydration sequence to install the chromanone, and an auxiliary-mediated diastereoselective reductive amination.
- Bellizzi, Mary E.,Bhatia, Ashok V.,Cullen, Steven C.,Gandarilla, Jorge,Kruger, Albert W.,Welch, Dennie S.
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p. 303 - 309
(2014/03/21)
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- New reactions of N-tert-butylimines; Formation of N-heterocycles by methyl radical elimination on flash vacuum thermolysis of N-benzylidene- and N-(2-pyridylmethylidene)-tert-butylamines
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Thermal reactions of N-benzylidene- and N-(2-pyridylmethylidene)-tert- butylamines (5 and 13) under FVT conditions have been investigated. Unexpectedly, at 800 °C, compound 5 yields 1,2-dimethylindole and 3-methylisoquinoline. In the reaction of 13 at 800 °C, 3-methylimidazo[1,5- a]pyridine was obtained as the major product. Mechanisms of these reactions have been proposed on the basis of DFT calculations. Furthermore, UV-photoelectron spectroscopy combined with FVT has been applied for direct monitoring and characterization of the thermolysis products in situ. Copyright
- Vu, Thien Y,Chrostowska, Anna,Huynh, Thi Kieu Xuan,Khayar, Said,Dargelos, Alain,Justyna, Katarzyna,Pasternak, Beata,Lesniak, Stanislaw,Wentrup, Curt
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supporting information
p. 14983 - 14988
(2013/11/06)
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- Acceptorless dehydrogenation of nitrogen heterocycles with a versatile iridium catalyst
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Gas up: A cyclometalated iridium complex is found to catalyze the dehydrogenation of various benzofused N-heterocycles, thus releasing H 2. Driven by as low as 0.1 mol % catalyst, the reaction affords quinolines, indoles, quinoxalines, isoquinolines, and β-carbolines in high yields. Copyright
- Wu, Jianjun,Talwar, Dinesh,Johnston, Steven,Yan, Ming,Xiao, Jianliang
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supporting information
p. 6983 - 6987
(2013/07/26)
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- Synthesis of 6-methyl-8H-dibenzo[a,g]quinolizin-8-imines via Reissert compounds
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Alkylation of Reissert compounds derived from 3-methylisoquinolines with several 2-cyanobenzylbromides followed by hydrolytic cleavage provided the corresponding 1-benzyl-3-methylisoquinolines. Treatment of the latter with methylmagnesiumiodide caused cyclization to the title compounds rather than formation of 2-acetylbenzylisoquinolines.
- Reimann, Eberhard,Hertel, Rainer,Krauss, Juergen
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experimental part
p. 673 - 684
(2009/07/18)
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- A One-Pot Isoquinoline Synthesis by Cyclodehydrogenation of N-Benzyl-α-alkylaminoacetals with Chlorosulfonic Acid: Formation of 3-Alkylisoquinolines
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A direct preparation of fully aromatized 3-alkylisoquinolines (3e-p), was achieved by cyclodehydrogenation with chlorosulfonic acid of N-benzyl-α-alkylaminoacetals (2e-p) which were prepared by addition of Grignard reagent to N-benzyliminoacetals (1a-d). Keywords --- N-benzyl-α-alkylaminoacetal; N-(3,4-dimethoxybenzyl)-α-alkylaminoacetal; N-(3-methoxybenzyl)-α-alkylaminoacetal; N-(4-methylbenzyl)-α-alkylaminoacetal; alkyl halide; 3-alkylisoquinoline; benzyliminoacetal; chlorosulfonic acid
- Kido, Kazuko,Watanabe, Yasuo
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p. 4964 - 4966
(2007/10/02)
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- ELECTROOXIDATIVE REARRANGEMENT OF TOSYLAMINO GROUP: FACILE SYNTHESIS OF α-AMINO ALDEHYDES FROM PRIMARY AMINES
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Anodic axidation of primary N-tosylamines in methanol containing halide ion gave α-(N-tosylamino) aldehyde dimethyl acetals, synthetically useful intermediates equivalent to α-amino aldehydes.
- Shono, Tatsuya,Matsumura, Yoshihiro,Katoh, Susumu,Inoue, Kenji,Matsumoto, Yonetatsu
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p. 6083 - 6086
(2007/10/02)
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- THERMOLYTIC RING OPENING OF ACYLOXYBENZOCYCLOBUTENES: AN EFFICIENT ROUTE TO 3-SUBSTITUTED ISOQUINOLINES
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Upon flash vacuum pyrolysis acyloxybenzocyclobutenes 4 rearrange through an intramolecular 1,5-acyl shift to 2-formylbenzyl ketones 6 which can be converted to 3-substituted isoquinolines 7.
- Schiess, Peter,Huys-Francotte, Martine,Vogel, Caspar
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p. 3959 - 3962
(2007/10/02)
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- STUDIES ON SRN1 REACTIONS - 9 A NEW ACCESS TO THE ISOQUINOLINE RING SYSTEM
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The SRN1 reaction between o-halogeno-benzylamines and enolates derived from a series of ketones and aldehydes affords 1, 2 dihydro-isoquinolines from which are obtained (i) the isoquinoline derivatives, either spontaneously or by treatment on Pd-C and (ii) the 1, 2, 3, 4 tetrahydro-isoquinoline derivatives after sodium borohydride reduction.
- Beugelmans, Rene,Chastanet, Jacqueline,Roussi, Georges
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p. 311 - 314
(2007/10/02)
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- REACTION OF BENZYL KETONES WITH NITRILES IN PRESENCE OF POCl3
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The reaction of benzyl ketones with nitriles in presence of POCl3 has been examined.It has been found that intermediate N-styrylimidoyl dichlorophosphates formed under reaction conditions undergo further reactions to isoquinoline and pyrimidine derivatives and form the products of fragmentation and condensation.The effect of structure of the substrates on the relative ratios of the products formed has been discussed.
- Zielinski, Wojciech
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- NOUVELLE SYNTHESE DU SQUELETTE DIHYDRO-1,2 ISOQUINOLEINE PAR REACTION DE SUBSTITUTION NUCLEOPHILE RADICALAIRE EN CHAINE (SRN1)
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The SRN1 reaction between ortho-iodo-benzylamine and ketone enolates affords the 1,2-dihydroisoquinoline ring system from which the 3-substituted isoquinolines or the 1,2,3,4-tetrahydroisoquinoline are obtained.
- Beugelmans, R.,Chastanet, J.,Roussi, G
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p. 2313 - 2314
(2007/10/02)
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- A NEW PHOTOCHEMICAL SYNTHETIC ROUTE TO 2,3-BENZODIAZEPINES FROM ISOQUINOLINE N-IMIDES
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Photolysis of the isoquinoline N-imides (6) under a basic condition gave the corresponding 5H-2,3-benzodiazepines (7), which were converted to the 3-acetyl-3H-2,3-benzodiazepines (11) by treatment with acetic anhydride.
- Enkaku, Michiko,Kurita, Jyoji,Tsuchiya, Takashi
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p. 1923 - 1926
(2007/10/02)
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- Recyclization of 3-Alkyl- and 1,3-Dialkylisoquinolinium Salts to Naphthylamines
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3-Methyl- and 3-benzylisoquinolinium salts undergo rearrangement to 2-alkylaminonaphthalenes under the influence of alcohol solutions of alkylamines.The rearrangement of 1,3-dimethyl- and 1-methyl-3-benzylisoquinolinium salts leads to both 1- and 2-alkylaminonaphthalenes with predominance of the former.
- Kost, A. N.,Terenin, V. I.,Yudin, L. G.,Sagitullin, R. S.
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p. 965 - 969
(2007/10/02)
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