- Zirconium Metal-Organic Frameworks Assembled from Pd and Pt PNNNP Pincer Complexes: Synthesis, Postsynthetic Modification, and Lewis Acid Catalysis
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Carboxylic acid-functionalized Pd and Pt PNNNP pincer complexes were used for the assembly of two porous Zr metal-organic frameworks (MOFs), 2-PdX and 2-PtX. Powder X-ray diffraction analysis shows that the new MOFs adopt cubic frame
- Reiner, Benjamin R.,Mucha, Neil T.,Rothstein, Anna,Temme, J. Sebastian,Duan, Pu,Schmidt-Rohr, Klaus,Foxman, Bruce M.,Wade, Casey R.
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- Iron-Catalyzed Intramolecular Aminations of C(sp3)?H Bonds in Alkylaryl Azides
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The nucleophilic iron complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]) catalyzes the direct intramolecular amination of unactivated C(sp3)?H bonds in alkylaryl azides, which results in the formation of substituted indoline and tetrahydroquinoline derivatives.
- Alt, Isabel T.,Guttroff, Claudia,Plietker, Bernd
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supporting information
p. 10582 - 10586
(2017/08/22)
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- New route to 2-substituted indoles by pyrolysis of N-acylacetylphenylhydroxylamines
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Convenient and regiospecific synthesis of 2-substituted indol (3) by thermolysis of N-acylacetylphenylhydroxylamine (1) and its mechanism including the formation of a radical intermediate are reported.
- Hirao,Mohri,Yonemitsu,Tabata,Sohma
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p. 1459 - 1462
(2007/10/02)
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- Functionalization of the Methyl Group of 2-Methylindole by Direct Generation of a C,N-Dianion
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The first method for directly generating C,N-dianion from an alkyl-substituted ?-excessive N-heterocyclic compound (2-methylindole) has been developed.It involves treatment with 3 equiv. of BuLi and 2 equiv. of ButOK in a particular sequence and results in the functionalization of the 2-methyl group of the indole in a regiospecific manner.
- Inagaki, Satoshi,Nishizawa, Yoshihiro,Sugiura, Takashi,Ishihara, Hideharu
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p. 179 - 180
(2007/10/02)
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- SYNTHESIS OF ALKYLINDOLES IN GAS PHASE ON AN ALUMINIUM ORTHOPHOSPHATE
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The synthesis of alkylindoles in the gas phase over an aluminium orthophosphate Kearby type catalyst has been studied.As reactants different carbonyl compounds and phenylhydrazine or aniline have been employed.The conditions of temperature and molar ratio of carbonyl compoud/nitrogenous compound have been changed.The best results were reached in the reactions between the lower aldehydes and aniline.Thus, 75 percent alkylindoles were obtained from propanaldehyde and 62 percent from butyraldehyde.Also remarkable is the reaction between cyclopentanone and phenylhydrazine because 45 percent 2,3-trimethyleneindole was obtained.
- Esteban, S.,Marinas, J. M.,Martinez-Alcazar, M. P.,Martinez, M.,Agarrabeitia, A. R.
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p. 715 - 720
(2007/10/02)
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- MELDRUM'S ACID IN ORGANIC SYNTHESIS 3. SYNTHESIS OF 2-SUBSTITUTED INDOLES FROM PHENYLHYDROXYLAMINE
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Treatment of phenylhydroxylamine oxalate with acyl Meldrum's acids in boiling acetonitrile readily gave N-acylacetylphenylhydroxylamines, which were converted to 2-substituted indoles by another treatment with acyl Meldrum's acids in refluxing toluene.N-B
- Mohri, Kunihiko,Oikawa, Yuji,Hirao, Ken-ichi,Yonemitsu, Osamu
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p. 515 - 520
(2007/10/02)
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- Meldrum's Acid in Organic Synthesis. VI. Synthesis of 2-Substituted Indoles from Acyl Meldrum's Acids and Phenylhydroxylamine via Sigmatropic Rearrangement
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Phenylhydroxylamine (13) oxalate was quite easily acylacetylated by heating with an equimolar amount of acyl Meldrum's acid (4) in acetonitrile to give an N-acylacetylphenylhydroxylamine (14) in high yield.When 14 was treated with another equimolar amount of the same 4 in refluxing toluene, a series of reactions, O-acylacetylation, 1-aza-1'-oxasigmatropic rearrangement, decarboxylation, dehydrative cyclization, and deacylation, occured consecutively to give a 2-substituted indole (16) in fair yield, though sometimes accompanied by the formation of a 5-substituted 4-isoxazolin-3-one (17).N-Benzoyl, N-acetyl, and N-benzyloxycarbonyl derivatives of phenylhydroxylamine (18) were treated with phenylacetyl Meldrum's acid (4i) in refluxing benzene containing copper powder to give readily rearranged ortho alkylation products (19), which were converted to the corresponding N-acyl-2-benzylindoles (20) by treatment with hydrochloric acid in boiling ethanol or with anhydrous p-toluenesulfonic acid in benzene at room temperature.Keywords - acyl Meldrum's acid; phenylhydroxylamine; N-acylacetylphenylhydroxylamine; 2-substituted indole; 1-aza-1'-oxasigmatropic rearrangement; acid-catalyzed cyclization
- Mohri, Kunihiko,Oikawa, Yuji,Hirao, Ken-ichi,Yonemitsu, Osamu
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p. 3097 - 3105
(2007/10/02)
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