346689-44-9Relevant academic research and scientific papers
Gold-catalyzed oxidative cyclization of amide-alkynes: access to functionalized γ-lactams
Zheng, Yi,Zhang, Ting-Ting,Shen, Wen-Bo
supporting information, p. 9688 - 9691 (2021/12/01)
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.
Lewis Acid Catalyzed Atom-Economic Synthesis of C2-Substituted Indoles from o-Amido Alkynols
Garkhedkar, Amol Milind,Gore, Babasaheb Sopan,Hu, Wan-Ping,Wang, Jeh-Jeng
supporting information, p. 3531 - 3536 (2020/04/20)
Herein we have disclosed a Zn(OTf)2 catalyzed synthesis of C2-alkyl substituted indole derivatives via unprecedented carbonyl group migration from o-amido alkynols. The key features of this protocol involve N,O-carbonyl group migration, broad s
One-pot preparation of 2-(alkyl)arylbenzoselenazoles from the corresponding N-(acetyl)benzoyl-2-iodoanilines via a microwave-assisted methodology
Redon, Sébastien,Kabri, Youssef,Crozet, Maxime D.,Vanelle, Patrice
supporting information, p. 5052 - 5054 (2015/01/09)
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.
Iodine-catalyzed, stereo- and regioselective synthesis of 4-arylidine-4H-benzo[d][1,3]oxazines and their applications for the synthesis of quinazoline 3-oxides
Lee, Wen-Chun,Shen, Ho-Chuan,Hu, Wan-Ping,Lo, Wei-Sheng,Murali, Chebrolu,Vandavasi, Jaya Kishore,Wang, Jeh-Jeng
, p. 2218 - 2228 (2012/11/07)
4-Benzylidene-2-aryl-4H-benzo[d][1,3] oxazines have been synthesized with high stereoselectivity and regioselectivities from 2-alkynylbenzamides in the presence of a catalytic amount of I2. In the reaction mechanism, iodine plays a key role in
Parallel synthesis of a library of benzoxazoles and benzothiazoles using ligand-accelerated copper-catalyzed cyclizations of ortho-halobenzanilides
Evindar, Ghotas,Batey, Robert A.
, p. 1802 - 1808 (2007/10/03)
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.
