Copper‐Catalyzed Selective Synthesis of Isoindolin‐1‐ones and Isoquinolin‐1‐ones from the Three‐Component Coupling of 2‐Halobenzoic Acid, Alkynylcarboxylic Acid and Ammonium Acetate

Irudayanathan, Francis Mariaraj; Noh, Jieun; Choi, Jinseop; Lee, Sunwoo

doi:10.1002/adsc.201400451

Cited by 38 publications

(17 citation statements)

References 65 publications

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“…Employing benzoic acids 10 ortho -substituted with iodine along with alkynylcarboxylic acids 11 and ammonium acetate ( 12 ), in the presence of caesium carbonate and copper iodide as catalyst (10%), a series of 3-methyleneisoindolin-1-ones 13 were obtained (Scheme 2) [77]. Several aromatic and heteroaromatic substituents can be introduced in the exocyclic methylene position with high regioselectivity.…”

Section: Reviewmentioning

confidence: 99%

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

Marigorta

Santos

Retana

et al. 2019

Beilstein J. Org. Chem.

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Benzo-fused γ-lactam rings such as isoindolin-2-ones and 2-oxindoles are part of the structure of many pharmaceutically active molecules. They can be often synthesized by means of multicomponent approaches and recent contributions in this field are summarized in this review. Clear advantages of these methods include the efficiency in saving raw materials and working time. However, there is still a need of new catalytic systems to allow the enantioselective preparation of these heterocycles by multicomponent reactions.

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Section: Reviewmentioning

confidence: 99%

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

Marigorta

Santos

Retana

et al. 2019

Beilstein J. Org. Chem.

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“…Щоправда, у роботі [29] синтез ізохіноліну 17 із 3-фенілізокумарину 16 за допомогою ацетату амонію проводили під високим тиском впродовж 6 год у розчині ДМСО та з додаванням каталізаторів (рис. 15).…”

Section: рис 13 формамід у синтезі 3-арилізохінолонів із 3-арилізокunclassified

Using of 3-Arylisocoumarins in 3-Arylisoquinolons Synthesis

Shablykina

Москвина

Савченко

et al. 2017

Bull. T. Shevchenko Nat. Univ. Kyiv. Chem.

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The review systematizes and analyzes the literature data (100 sources) regarding the recyclization of 3-arylisocoumarins (3-aryl-1H-isochromen-1-ones) under the action of primary N-nucleophiles that leads to the formation of 3-arylisoquinolones (3-arylisoquinolin-1(2H)-ones). This reaction may be carried out with a wide range of primary aminogroup-containing compounds: ammonia, primary aliphatic, aromatic, and heteroaromatic amines, hydrazine, and hydroxylamine. This transformation is not hindered by the presence of active functional groups (hydroxyl, acetal, carboxyl, ester, nitrile groups, or additional aminogroup) neither in 3-arylcoumarin nor in the primary amine. A special attention has been paid to reaction conditions (temperature regime, duration, solvent, catalysts), which may vary greatly. In particular, it is pointed out that in most cases to carry out high-temperature recyclization of 3-arylisocoumarins with ammonia and volatile amines with low molecular weight the use of closed reactors and high-pressure flasks was required. The cases of successful recyclization of 11,12-dihydrodibenzo[c,h]chromen-6-ones, indeno[1,2-c]isochromen-5(11H)-ones, isochromeno[4,3-c]chromen-6,11-dione and 5H-benzofuro[3,2-c]isochromen-5-one are reviewed separately. The polycondensated heterocyclic system of these compounds contains a 3-arylisocoumarin fragment. The biological activity data is presented for the compounds obtained via this transformation – 3-arylisoquinolin-1(2H)-ones, and also polycondensated systems that contain this fragment, e.g. 11,12-dihydrobenzo[c]phenanthridin-6(5H)-ones and 6H-indeno[1,2-c]isoquinoline-5,11-diones. The opportunities to use 3-arylisoquinolin-1(2H)-ones in the synthesis of other compounds of isoquinoline family, e.g. natural benzo[c]phenanthridinealocoloids, are demonstrated.

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“…Methods that use palladium catalysts such as Heck, Sonagashira, and Suzuki were also found to be the effective methods to synthesize isoindolinone . Very recently, we reported the three component coupling reactions of 2‐halobenzoic acid, alkynyl carboxylic acid, and NH 4 OAc for the synthesis of isoindolinones in the presence of commercially cheap copper catalyst and cesium carbonate as base . Usage of aryl alkynyl carboxylic acids ensured safe handling and they were easily prepared from a one‐step coupling reaction involving a simple isolation protocol .…”

Section: Optimization Of the Reaction Conditionmentioning

confidence: 99%

“…6 Very recently, we reported the three component coupling reactions of 2-halobenzoic acid, alkynyl carboxylic acid, and NH 4 OAc for the synthesis of isoindolinones in the presence of commercially cheap copper catalyst and cesium carbonate as base. 7 Usage of aryl alkynyl carboxylic acids ensured safe handling and they were easily prepared from a one-step coupling reaction involving a simple isolation protocol. 8 However, 2-halobenzoic acids were limited to 2-iodo-and 2-bromobenzoic acids in the previous report.…”

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confidence: 99%

Copper‐catalyzed One‐Pot Synthesis of Isoindolinones from 2‐Chlorobenzoic Acid, Aryl Alkynyl Carboxylic Acid, and Ammonium Acetate

Irudayanathan

Lee

2015

Bulletin Korean Chem Soc

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Copper‐Catalyzed Selective Synthesis of Isoindolin‐1‐ones and Isoquinolin‐1‐ones from the Three‐Component Coupling of 2‐Halobenzoic Acid, Alkynylcarboxylic Acid and Ammonium Acetate

Abstract: An efficient one‐pot synthesis of isoindolin‐1‐ones is described starting from 2‐iodobenzoic acid and arylalkynylcarboxylic acid or 2‐propinoic acid in the presence of ammonium acetate [cf.

Cited by 38 publications

References 65 publications

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

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

Using of 3-Arylisocoumarins in 3-Arylisoquinolons Synthesis

Copper‐catalyzed One‐Pot Synthesis of Isoindolinones from 2‐Chlorobenzoic Acid, Aryl Alkynyl Carboxylic Acid, and Ammonium Acetate

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