- Dibrominative Spirocyclization of 2-Butynolyl Anilides: Synthesis of gem-Dibromospirocyclic Benzo[ d][1,3]oxazines and Their Application in the Synthesis of 4 H-Furo[3,2- b]indoles
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The combination of catalytic aqueous hydrochloric acid (HCl) and N-bromosuccinimide (NBS) generated electrophilic bromine monochloride (BrCl), which readily induced spiroannulation of 2-alkynolyl anilides (n = 1-3) to form gem-dibromospirocyclic benzo[d][
- Chaisan, Nattawadee,Ruengsangtongkul, Sureeporn,Tummatorn, Jumreang,Ruchirawat, Somsak,Chainok, Kittipong,Thongsornkleeb, Charnsak
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p. 4671 - 4698
(2021/04/06)
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- Aniline-Type Hypervalent Iodine(III) for Intramolecular Cyclization via C?H Bond Abstraction of Hydrocarbons Containing N- and O-Nucleophiles
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We developed a method for the preparation of (diacetoxyiodo)-2-(N-alkylamido)benzene as an aniline-type hypervalent iodine(III). We also achieved direct cyclizations via C?H bond abstraction, such as the Hofmann-L?ffler-Freytag reaction, a direct amination, and a direct lactonization, using the aniline-type hypervalent iodine(III) to obtain corresponding products in high yields. (Figure presented.).
- Nishiguchi, Yuna,Moriyama, Katsuhiko
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p. 3354 - 3358
(2021/05/17)
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- Gold-catalyzed oxidative cyclization of amide-alkynes: access to functionalized γ-lactams
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An efficient gold-catalyzed oxidative cyclization of amide-alkynes is developed. A series of functionalized γ-lactams are easily accessed by employing this strategy. The tandem reaction proceeds through alkyne oxidation, carbene/alkyne metathesis, and donor/donor carbene oxidation.
- Zheng, Yi,Zhang, Ting-Ting,Shen, Wen-Bo
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supporting information
p. 9688 - 9691
(2021/12/01)
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- Intermolecular coupling of 2-iodoanilides with benzoxazoles: Synthesis of N-(2-Benzoxazol-2-ylphenyl)benzamides via C-H activation
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Using CuI/xantphos/Pd(OAc)2 catalytic system, the intermolecular C-C cross coupling between benzoxazoles and ortho-haloanilides has been developed in moderate to good yields. The procedure tolerates a series of functional groups on benzoxazole, such as ester, chloro, methyl, and methoxy groups. This divergent approach provides access to various N-(2-Benzoxazol-2-ylphenyl)amides.
- Sasmal, Swarnendu,Sen, Indira,Hall, Roger G.,Pal, Sitaram
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supporting information
p. 1374 - 1377
(2015/03/04)
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- One-pot preparation of 2-(alkyl)arylbenzoselenazoles from the corresponding N-(acetyl)benzoyl-2-iodoanilines via a microwave-assisted methodology
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We report here the first example of a one-pot synthesis of 2-(alkyl)arylbenzoselenazoles from N-(acetyl)benzoyl-2-iodoanilines. The reaction was carried out in the presence of Woollins' reagent under microwave irradiation and resulted in moderate to good yields.
- Redon, Sébastien,Kabri, Youssef,Crozet, Maxime D.,Vanelle, Patrice
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supporting information
p. 5052 - 5054
(2015/01/09)
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- Cu-catalyzed in situ generation of thiol using xanthate as a thiol surrogate for the one-pot synthesis of benzothiazoles and benzothiophenes
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A new copper-catalyzed in situ generation of aryl thiolates strategy was successfully developed for the one-pot synthesis of substituted benzothiazoles from 2-iodoanilides using xanthate as a thiol precursor. A wide range of 2-iodoanilides with both electron-releasing and electron-withdrawing groups produced the corresponding benzothiazoles in good yields. Further, this one-pot protocol was successfully utilized for the synthesis of a potent antitumor agent 2-(3,4-dimethoxyphenyl)-5-fluorobenzo[d]thiazole (PMX 610). Finally, the copper-catalyzed in situ generation of aryl thiolates strategy was successfully applied for the domino synthesis of substituted benzothiophenes from o-haloalkynyl benzenes using xanthate as a thiol precursor.
- Prasad,Sekar
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supporting information
p. 1659 - 1665
(2013/03/28)
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- Iron-catalyzed aryl-aryl cross-coupling reaction tolerating amides and unprotected quinolinones
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The iron(III)-catalyzed cross-coupling reaction between functionalized arylcopper reagents and aromatic iodides bearing an amide function or an unprotected quinolinone leads smoothly to polyfunctionalized biphenyls in excellent yields due to an intramolec
- Kofink, Christiane C.,Blank, Benoit,Pagano, Sandro,Goetz, Nadine,Knochel, Paul
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p. 1954 - 1956
(2008/02/07)
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- Parallel synthesis of a library of benzoxazoles and benzothiazoles using ligand-accelerated copper-catalyzed cyclizations of ortho-halobenzanilides
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A general method for the formation of benzoxazoles via a copper-catalyzed cyclization of ortho-haloanilides is reported. This approach complements the more commonly used strategies for benzoxazole formation which require 2-aminophenols as substrates. The reaction involves an intramolecular C-O cross-coupling of the ortho-haloanilides and is believed to proceed via an oxidative insertion/reductive elimination pathway through a Cu(I)/Cu(III) manifold. The reaction is also applicable to the formation of benzothiazoles. A variety of ligands including 1,10-phenanthroline and N,N′- dimethylethylenediamine were shown to provide ligand acceleration/stabilization in the reaction. Optimal conditions for cyclization used a catalyst combination of CuI and 1,10-phenanthroline (10 mol %). The method was amenable to a parallel-synthesis approach, as demonstrated by the synthesis of a library of benzoxazoles and benzothiazoles substituted at various positions in the ring. Most examples utilized the cyclization of ortho-bromoanilides, but orthoiodoanilides and ortho-chloroanilides also undergo a reaction under these conditions. The rate of reaction of the ortho-haloanilides follows the order I > Br > Cl, consistent with oxidative addition being the rate-determining step.
- Evindar, Ghotas,Batey, Robert A.
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p. 1802 - 1808
(2007/10/03)
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