Synthesis Of Isocoumarins Research Articles

ChemInform Abstract: K2CO3‐Promoted Domino Reactions for Synthesis of Isocoumarins under Microwave Irradiation.

AbstractA small library of isocoumarin derivatives has been synthesized via K2CO3-catalyzed domino reactions of 2-carboxybenzaldehyde and ω-bromoacetophenones under microwave irradiation (MW). This strategy offers a simple, environmentally acceptable route to synthesize isocoumarin derivatives in moderate to excellent yields. All new compounds were characterized by 1H NMR, 13C NMR, infrared, and high-resolution mass spectroscopic techniques.

ChemInform Abstract: A Simple and Efficient Synthesis of Isocoumarins and Alkylidenephthalides from 3‐(1‐Hydroxycarbethoxy/alkyl)phthalides with a DEAD/PPh3/TBHP System.

AbstractA facile and novel approach to the synthesis of isocoumarins and alkylidenephthalides under similar conditions is described.

ChemInform Abstract: Synthesis of Isocoumarins Through Three‐Component Couplings of Arynes, Terminal Alkynes, and Carbon Dioxide Catalyzed by an NHC‐Copper Complex.

AbstractThe use of aliphatic alkynes such as (Vb) is less suitable and even a change in catalyst does not increase the yield significantly.

ChemInform Abstract: Synthesis of Isocoumarins with Different Substituted Patterns via Passerini—Aldol Sequence.

AbstractThe three component reactions of 2‐formylbenzoic acid, arylglyoxals, and isocyanides allow the synthesis of different substituted isocoumarins by a simple change of the solvent.

K2CO3-Promoted Domino Reactions for Synthesis of Isocoumarins Under Microwave Irradiation

A small library of isocoumarin derivatives has been synthesized via K2CO3-catalyzed domino reactions of 2-carboxybenzaldehyde and ω-bromoacetophenones under microwave irradiation (MW). This strategy offers a simple, environmentally acceptable route to synthesize isocoumarin derivatives in moderate to excellent yields. All new compounds were characterized by 1H NMR, 13C NMR, infrared, and high-resolution mass spectroscopic techniques.

Synthesis of Isocoumarins: Rhenium Complex-Catalyzed Cyclization of 2-Ethynylbenzoic Acids

Synthesis of Isocoumarins: Rhenium Complex-Catalyzed Cyclization of 2-Ethynylbenzoic Acids

Ruthenium-catalyzed decarbonylative addition reaction of anhydrides with alkynes: a facile synthesis of isocoumarins and α-pyrones.

A novel ruthenium catalyzed straightforward and efficient synthesis of isocoumarin and α-pyrone derivatives has been accomplished by the decarbonylative addition reaction of anhydrides with alkynes under thermal conditions.

ChemInform Abstract: Chiron Based Synthesis of Isocoumarins: Reactivity of α‐Substituted Carboxylic Acids.

AbstractHomophthalic acid is coupled with various (S)‐protected amino acid chlorides, but only for substrate (I) the target isocoumarin can be isolated.

Synthesis of isocoumarins with different substituted patterns via Passerini-aldol sequence.

An efficient combination between the Passerini three-component reaction and aldol condensation has been developed for the synthesis of bicyclic isocoumarins with different substituted patterns via solvent-dependent domino pathways. These two operationally friendly methods simultaneously install C–O and C–C bonds in a one-pot manner, allowing the utilization of low-cost and readily accessible 2-formylbenzoic acid, isocyanides, and arylglyoxals. Mechanisms of formation of different substituted isocoumarin derivatives are also proposed.

Synthesis of Isocoumarins through Three‐Component Couplings of Arynes, Terminal Alkynes, and Carbon Dioxide Catalyzed by an NHC–Copper Complex

AbstractA copper‐catalyzed multicomponent coupling reaction between in situ generated ortho‐arynes, terminal alkynes, and carbon dioxide was developed to access isocoumarins in moderate to good yields. The key to this CO2‐incorporating reaction was the use of a versatile N‐heterocyclic carbene/copper complex that was able to catalyze multiple transformations within the three‐component reaction.

Synthesis of isocoumarins through three-component couplings of arynes, terminal alkynes, and carbon dioxide catalyzed by an NHC-copper complex.

A copper-catalyzed multicomponent coupling reaction between in situ generated ortho-arynes, terminal alkynes, and carbon dioxide was developed to access isocoumarins in moderate to good yields. The key to this CO2-incorporating reaction was the use of a versatile N-heterocyclic carbene/copper complex that was able to catalyze multiple transformations within the three-component reaction.

Chiron based synthesis of isocoumarins: reactivity of α-substituted carboxylic acids

The asymmetric synthesis of a novel (S)-isocoumarin has been attempted in a single step by the coupling of homophthalic acid with (S)-N-protected amino acids and α-chloroacids at high temperature by exploiting a chiral pool methodology. The coupling of homophthalic acid with N-protected (S)-amino acids gave exclusion of the carboxyl/alkyl group. However, coupling of homophthalic acid with α-chloroacids afforded asymmetric isocoumarins in high yield.

ChemInform Abstract: Regioselective One‐Pot Synthesis of Isocoumarins and Phthalides from 2‐Iodobenzoic Acids and Alkynes by Temperature Control.

AbstractOptimized conditions are developed for the coupling reaction of 2‐iodobenzoic acid with various alkynes.

ChemInform Abstract: Palladium(II)‐Catalyzed Tandem Annulation Reaction of o‐Alkynylbenzoates with Methyl Vinyl Ketone for the Synthesis of Isocoumarins.

A palladium(II)-catalyzed highly regioselective tandem reactions of o-alkynylbenzoates with methyl vinyl ketone for the synthesis of isocoumarins was developed. It is a convenient, mild and environmentally benign reaction with moderate to high yield. The

Regioselective One‐Pot Synthesis of Isocoumarins and Phthalides from 2‐Iodobenzoic Acids and Alkynes by Temperature Control

AbstractCopper‐catalyzed coupling reaction of 2‐iodobenzoic acids and alkynes such as terminal acetylenes, alkynyl carboxylic acids, and trimethylsilylacetylene selectively afforded isocoumarins and phthalides in the presence of cesium carbonate (Cs2CO3) and dimethyl sulfoxide (DMSO). Among the regioselective products, only the 6‐endo‐dig product, isocoumarin, was formed at 100 °C, and the 5‐exo‐dig product, phthalide, was formed as a major product at 25 °C. A variety of alkynes produced the corresponding isocoumarins and phthalides in good yields. A mechanism is suggested in which the formation of 2‐alkynylbenzoic acid as an intermediate via Sonogashira‐type coupling was ruled out in the reaction pathway.magnified image

Palladium(II)-catalyzed tandem annulation reaction of o-alkynylbenzoates with methyl vinyl ketone for the synthesis of isocoumarins

A palladium(II)-catalyzed highly regioselective tandem reactions of o-alkynylbenzoates with methyl vinyl ketone for the synthesis of isocoumarins was developed. It is a convenient, mild and environmentally benign reaction with moderate to high yield. The reaction is initiated by the Pd(II) species and regenerate the Pd(II) species to complete the catalytic cycle without the necessity of a redox system.

Tandem Michael Addition/Cyclization Reaction of 2,3-Allenoates with Organozincs: Facile Synthesis of Isocoumarins

A series of isocoumarin derivatives have been synthesized via the reaction of 2-(o-(methoxycarbonyl)phenyl)-2,3-allenoates with organozincs in CH2Cl2 at room temperature (for dialkylzinc) or 100 °C (for Ph2Zn) through a tandem Michael addition/intramolecular cyclization process.

ChemInform Abstract: Super Acid Catalyzed Sequential Hydrolysis/Cycloisomerization of o‐(Acetylenic)benzamides under Microwave Condition: Synthesis, Antinociceptive and Antiinflammatory Activity of Substituted Isocoumarins.

AbstractThis is the first direct synthesis of isocoumarins from o‐alkynylbenzamides under super acid conditions.

ChemInform Abstract: Palladium‐Catalyzed Synthesis of Isocoumarins and Phthalides via tert‐Butyl Isocyanide Insertion.

AbstractThis is a simple and efficient method for the synthesis of isocoumarins and phthalides from easily accessible substrates in good yields.

ChemInform Abstract: Pd(II)‐Mediated Cyclization of o‐Allylbenzaldehydes in Water: A Novel Synthesis of Isocoumarins.

AbstractUnder optimized conditions using a copper salt in addition to the palladium catalyst and water as both reagent and solvent, high yields of the isocoumarins are obtained within an hour.