Efficient N-arylation of 4-chloroquinazolines en route to novel 4-anilinoquinazolines as potential anticancer agents

• Rodolfo H. V. Nishimura,
• Thiago dos Santos,
• Valter E. Murie,
• Luciana C. Furtado,
• Leticia V. Costa-Lotufo and
• Giuliano C. Clososki

Beilstein J. Org. Chem. 2021, 17, 2968–2975, doi:10.3762/bjoc.17.206

• . While anthranilamide (5) bromination with N-bromosuccinimide in acetonitrile at room temperature [29] furnished 2-amino-5-bromobenzamide (6a) in 78% yield, iodination of 5 with iodine in the presence of hydrogen peroxide in water [30] at 50 °C provided 2-amino-5-iodobenzamide (6b) in 89% yield. After

Palladium-catalyzed regio- and stereoselective synthesis of aryl and 3-indolyl-substituted 4-methylene-3,4-dihydroisoquinolin-1(2H)-ones

• Valeria Nori,
• Antonio Arcadi,
• Armando Carlone,
• Fabio Marinelli and
• Marco Chiarini

Beilstein J. Org. Chem. 2020, 16, 1084–1091, doi:10.3762/bjoc.16.95

• temperature (Scheme 2). Initially, we explored the reaction of the N-(4-(4-acetylphenyl)-2-methylbut-3-yn-2-yl)-N-benzyl-2-iodobenzamide (2a) with a variable excess of the phenylboronic acid (3a) in the presence of K3PO4 as the base (K3PO4: 3 equiv) by using 5 mol % of different palladium catalysts/solvent

• -iodobenzamide 2. Typical procedure for the preparation of-2-benzyl-3,4-dihydroisoquinolin-1(2H)-ones (4): preparation of (Z)-4-((4-acetylphenyl)(phenyl)methylene)-2-benzyl-3,3-dimethyl-3,4-dihydroisoquinolin-1(2H)-one (4aa): To a stirred solution (0.2 M) of N-(4-(4-acetylphenyl)-2-methylbut-3-yn-2-yl)-N-benzyl

• -2-iodobenzamide (2a, 100 mg, 0.19 mmol) in EtOH (1 mL), were added phenylboronic acid (3a, 34.7 mg, 0.285 mmol) and K3PO4 (120.9 mg, 0.57 mmol); after 5 min stirring at room temperature, PdCl2 (2 mg, 0.0095 mmol) was added. The mixture was stirred at 79 °C under an N2 atmosphere and stirring was

Multicomponent reactions (MCRs): a useful access to the synthesis of benzo-fused γ-lactams

• Edorta Martínez de Marigorta,
• Jesús M. de Los Santos,
• Ana M. Ochoa de Retana,
• Javier Vicario and
• Francisco Palacios

Beilstein J. Org. Chem. 2019, 15, 1065–1085, doi:10.3762/bjoc.15.104

• derivatives do it through the carbon at 3-position. Although a quaternary stereocentre is created in the process, no attempts to make this synthesis in a stereoselective fashion were reported. A tentative mechanism is proposed, based in a Sonogashira coupling of iodobenzamide 17 and copper acetylide, in a

• three-component reaction of 2-iodobenzamide 17, terminal alkyne 18 and pyrrole or indole derivatives 19. Palladium-catalysed three-component reaction of ethynylbenzamides 21, secondary amines 22 and CO (23). Proposed mechanism for the formation of methyleneisoindolinones 24. Copper-catalysed three

Preparation, structure, and reactivity of bicyclic benziodazole: a new hypervalent iodine heterocycle

• Akira Yoshimura,
• Michael T. Shea,
• Cody L. Makitalo,
• Melissa E. Jarvi,
• Gregory T. Rohde,
• Akio Saito,
• Mekhman S. Yusubov and
• Viktor V. Zhdankin

Beilstein J. Org. Chem. 2018, 14, 1016–1020, doi:10.3762/bjoc.14.87

• heterocyclic ring. Benziodazoles 5 are usually prepared by the treatment of 2-iodobenzamide derivatives 4 with appropriate oxidants under mild conditions [31][32][33][34][35]. Derivatives of benziodazole can be used as reagents for various oxidative functionalizations of organic substrates [33][36]. For

2-Iodo-N-isopropyl-5-methoxybenzamide as a highly reactive and environmentally benign catalyst for alcohol oxidation

• Takayuki Yakura,
• Tomoya Fujiwara,
• Akihiro Yamada and
• Hisanori Nambu

Beilstein J. Org. Chem. 2018, 14, 971–978, doi:10.3762/bjoc.14.82

• to benzophenone in the presence of Oxone® (2KHSO5·KHSO4·K2SO4) as a co-oxidant at room temperature. A study on the substituent effect of the benzene ring of N-isopropyl-2-iodobenzamide on the oxidation revealed that its reactivity increased in the following order of substitution: 5-NO2 < 5-CO2Me, 3

• derivative at room temperature is a result of the rapid generation of the pentavalent species from the trivalent species during the reaction. 5-Methoxy-2-iodobenzamide would be an efficient and environmentally benign catalyst for the oxidation of alcohols, especially benzylic alcohols. Keywords: hypervalent

• iodine; iodobenzamide; organic catalysis; oxidation; oxone; Introduction The development of an efficient and environmentally benign organic synthesis is required for minimizing material use, energy consumption, and environmental pollution in the production of both bulk and fine chemicals. Oxidation is a