- Synthesis of polyheterocyclic ring compounds by the intramolecular cycloaddition of N-alkenyl substituted diazoimides Albert Padwa
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Rhodium(II) catalysis of various diazoimides containing tethered π-systems attached to the nitrogen atom results in isomuenchnone dipole formation followed by intramolecular dipolar-cycloaddition.
- Austin, David J.
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- Synthesis of functionalized indoles via palladium-catalyzed cyclization of N-(2-allylphenyl) benzamide: A method for synthesis of indomethacin precursor
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We developed an efficient method for synthesis of substituted N-benzoylindole via Pd(II)-catalyzed C-H functionalization of substituted N-(2-allylphenyl)benzamide. The reaction showed a broad substrate scope (including N-acetyl and N-Ts substrates) and substituted indoles were obtained in good to excellent yields. The most distinctive feature of this method lies in the high selectivity for N-benzoylindole over benzoxazine, and this is the first example of Pd(II)-catalyzed synthesis of substituted N-benzoylindole. Notably, this new method was applied for the synthesis of key intermediate of indomethacin.
- Chang, Zhe,Dong, Zheng,Ma, Tong,Zhang, Yu,Zhao, Depeng,Zhao, Heng
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supporting information
(2020/03/19)
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- Indole compound and synthesizing and application methods thereof
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The invention relates to an indole compound and synthesizing and application methods thereof. The indole compound is prepared by selecting specific substituent groups. Experiments find that the indolecompound can achieve good inhibiting effects on prostatic cancer, good in drug-resistance-proofness and low in side effects when applied as an anti-cancer drug; besides, the synthesizing method of the indole compound comprises subjecting a compound with the structure shown as the formula (II), palladium acetate, benzoquinones and organic acids to reaction in solvent to obtain the indole compoundwith the structure shown as the formula (I). Experiment results show that the synthesizing method of the indole compound is low in requirements on substrate and high in product yield.
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Paragraph 0084-0087
(2019/10/22)
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- Green Organocatalytic Synthesis of Indolines and Pyrrolidines from Alkenes
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Employing a green and efficient 2,2,2-trifluoroacetophenone-catalyzed oxidation of alkenes, which utilizes H2O2 as the green oxidant, a novel and sustainable synthesis of indolines and pyrrolidines was developed. This constitutes a cheap, general and environmentally-friendly protocol for the synthesis of substituted nitrogen-containing heterocycles. A variety of substitution patterns, both aromatic and aliphatic moieties, are well tolerated leading to the desired nitrogen heterocycles in good to excellent yields. (Figure presented.).
- Theodorou, Alexis,Kokotos, Christoforos G.
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p. 1577 - 1581
(2017/05/05)
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- M-CPBA-Mediated Intramolecular Aminohydroxylation of N-Sulfonyl Aminoalkenes to Synthesize β-Hydroxyl Cyclic Amines
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A variety of structurally diverse N-sulfonyl-protected aminoalkenes readily reacted with m-CPBA to produce a series of β-hydroxyl cyclic amines in high yields through intramolecular aminohydroxylation. This metal-free and easy-to-handle synthetic methodol
- Yin, Yan,Zhou, Hong,Sun, Guofeng,Liu, Xichen
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p. 1337 - 1345
(2015/10/06)
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- Copper(II) carboxylate-promoted intramolecular carboamination of alkenes for the synthesis of polycyclic lactams
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The copper(II) carboxylate-promoted intramolecular carboamination reactions of variously substituted y-alkenyl amides have been investigated. These oxidative cyclization reactions efficiently provide polycyclic lactams, useful intermediates in nitrogen he
- Fuller, Peter H.,Chemler, Sherry R.
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p. 5477 - 5480
(2008/09/17)
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- A metal-free approach to the synthesis of indoline derivatives by a phenyliodine(III) bis(trifluoroacetate)-mediated amidohydroxylation reaction
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A novel approach to the synthesis of indoline derivatives is presented. The key cyclization step features the phenyliodine-(III) bis(trifluoroacetate)- (PIFA-) mediated formation of a N-acylnitrenium ion and its succeeding intramolecular trapping by the o
- Correa, Arkaitz,Tellitu, Imanol,Dominguez, Esther,SanMartin, Raul
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p. 8316 - 8319
(2007/10/03)
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- Studies on the intramolecular cycloaddition reaction of isomunchnones derived from N-alkenyl substituted diazoimides
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A series of N-alkenyl substituted diazoimides were prepared and subjected to Rh(II) catalyzed decomposition. The initially generated rhodium carbenoid undergoes ready cyclization onto the neighboring amide carbonyl oxygen atom to generate an isomunchnone
- Padwa,Austin,Price,Weingarten
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p. 3247 - 3260
(2007/10/03)
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- INTRAMOLECULAR CYCLIZATION USING METHYL(BISMETHYLTHIO)SULPHONIUM SALTS. PART 5. SYNTHESIS OF FUNCIONALIZED 4,5-DIHYDRO-3,1-BENZOXAZEPINES
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The reaction of methyl(bismethylthio)sulphonium hexachloroantimonate 1 with N-(2-allylphenyl)benzamide 2 gives the 4-methylthio-methyl-4,5-dihydro-3,1-benzoxazepine 4.Other electrophilic reagents reacts with 2 to give exclusively or preferentially product
- Capozzi, Giuseppe,Ottana, Rosaria,Romeo, Giovanni
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