- 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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- Synthesis, Biological Evaluation of ortho-Carboxamidostilbenes as Potential Inhibitors of Hyperglycemic Enzymes, and Molecular Docking Study
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A new series of ortho-carboxamidostilbenes derivatives were synthesized via Heck Coupling and screened for their α-amylase and α-glucosidase inhibitory potential. The results indicated that all the synthesized compounds showed a substantial α-glucosidase
- Abu Bakar, Mohamad Hafizi,Awang, Khalijah,Azmi, Mohamad Nurul,Che Omar, Mohammad Tasyriq,Mohamad, Norhadi,Phua, Yoong Hui,Supratman, Unang,Wahab, Habibah A.
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- Lewis Acid Catalyzed Atom-Economic Synthesis of C2-Substituted Indoles from o-Amido Alkynols
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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
- Garkhedkar, Amol Milind,Gore, Babasaheb Sopan,Hu, Wan-Ping,Wang, Jeh-Jeng
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supporting information
p. 3531 - 3536
(2020/04/20)
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- A Pd-catalyzed domino Larock annulation/dearomative Heck reaction
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A palladium-catalyzed domino Larock annulation/dearomative Heck reaction is developed, which delivers a range of tetracyclic indoline derivatives in moderate to excellent yields through a Larock annulation of N-bromobenzoyl o-iodoanilines with alkynes and a subsequent intramolecular dearomative Heck reaction. This protocol provides a straightforward route to structurally diverse indolines from readily available starting materials by forming two new rings and three chemical bonds in a single step.
- Liang, Ren-Xiao,Xu, Deng-Yun,Yang, Fu-Ming,Jia, Yi-Xia
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supporting information
p. 7711 - 7714
(2019/07/09)
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- Dibenzo[ b, e ]azepin-6-ones and Seven-Membered Sultam Derivatives: Convenient Synthesis via Palladium-Catalyzed Regioselective Intramolecular Heck Reaction and Application towards Drug-Like Small Molecules
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A new, convenient synthesis of dibenzo[ b, e ]azepin-6-ones and seven-membered sultam derivatives have been envisaged via Pd-catalyzed regioselective intramolecular Heck reaction of the corresponding easily accessible precursors. This protocol has been successfully implemented to synthesize N -methyldarenzepine in four steps and in good yield. Moreover, one of the intermediates has been utilized for the synthesis of a new analogue of darenzepine. Preliminary modeling studies were performed to investigate the binding potential to muscarinic acetylcholine receptor (M4).
- Ansary, Inul,Das, Arijit,Kundu, Mrinalkanti,Maiti, Arup,Roy, Kuldeep K.
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p. 3231 - 3240
(2019/08/28)
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- A Pd-catalyzed direct entry to 11-substituted 6H-isoindolo[2,1-a]indol-6-one derivatives as potential anticancer agents
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We describe Pd-mediated one-step synthesis of 11-substituted 6H-isoindolo[2,1-a]indol-6-ones via a sequential intramolecular Heck reaction of the corresponding dihalo N-allyl substituted N-arylbenzamide derivatives. Several of these compounds showed promi
- Nallapati, Suresh Babu,Adepu, Raju,Ashfaq, Mohd Ashraf,Sreenivas, B. Yogi,Mukkanti,Pal, Manojit
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p. 88686 - 88691
(2015/11/09)
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- A highly efficient copper-catalyzed method for the synthesis of 2-hydroxybenzamides in water
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An efficient copper-catalyzed synthetic method for the preparation of 2-hydroxybenzamides is described for the first time from 2-chlorobenzamide substrates using copper iodide/1,10-phenanthroline and a base, potassium hydroxide, in neat water. By using this reaction, a series of 2-hydroxybenzamides with functional groups such as fluoro, chloro, iodo, methoxy, amide, and alcohol have been obtained in 33-96% yield. Other aromatic 2-chloroarylamides such as naphthalene, pyridine, and thiophene are found to be equally compatible to the reaction. It is proposed that the reaction proceed via formation of copper-amide complex, which may facilitate the hydroxylation in water. Overall, the first report on copper-catalyzed hydroxylation reaction in water and first catalytic route for the synthesis of 2-hydroxybenzamides is presented. Simple purification procedure and convenience of employing low-cost reagents in neat water make this method practical and economical for the synthesis of 2-hydroxybenzamides. Georg Thieme Verlag Stuttgart · New York.
- Balkrishna, Shah Jaimin,Kumar, Sangit
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experimental part
p. 1417 - 1426
(2012/06/30)
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