Efficient synthesis of some 3-arylisoquinolin-1(2H)-ones

Abstract

A number of 3-arylisoquinolin-1(2H)-ones were efficiently prepared from the corresponding 3-arylisocoumarins by refluxing with methanamide.Keywords: isocoumarin, isoquinolin-1(2H)-one, methanamide.Isoquinolin-1(2H)-ones (isocarbostyrils) are the nitrogen analogues of isocoumarins (1H-2-benzopyran-1-ones). Various isoquinolin-1(2H)-one derivatives are found in several bioactive natural products such as thalifoline, doryphorine [1], ruprechstyril [2], narciclasine [3], pancretistatin, lycoricidine [4], alkaloids coryaldine [5], dorianine [6,7], hydroxyhydrastinine, and thalflavine [8]. The isoquinolone nucleus is also an integral part of complex isoquinoline alkaloids and is a useful building block in organic synthesis.The isoquinolone skeleton, biogenetically derived from the amino acid phenyl-alanine, exhibits biomimetic characteristics [9]. Substituted isoquinolones are orally effective antagonists of 5-HT 3 receptors, which have shown a high efficacy in the control of cancer models [10], thymidylate synthase (TS) inhibitors [11], human tumor necrosis factor (TNF) inhibitors, and tachykinin receptors [12]. Substituted isocarbostyrils exhibiting antidepressant [13], anti-inflammatory [14], analgesic [15], hypolipidemic [16], and analeptic [17] activities have also been reported.In view of the great therapeutic value of such motifs in various bioactive molecules, a number of synthetic routes have been developed. These include the Gabriel-Coleman synthesis [18], ring enlargement of phthalimides [19], condensation of amines with homophthalic anhydrides [20], reaction of 2-methoxycarbonylstyrene oxide with ammonia or methylamine [21], and reaction of coumarin and isocoumarin derivatives [22] with ammonia and amines. The latter method has been used in the synthesis of (±)-licoricidine [23], narciclasine [24], (+)-deoxypancretistatin [25], and the benzophenanthridine alkaloid nitidine [26]. In addition, the [4+2] cycloaddition of the ketenes to cyano ketones [27], treatment of indanones with sodium azide [28], recently reported solid-phase synthesis of isoquinolinones using Bischler-Napieralski cyclization [29], palladium-mediated synthesis of isoquinolinones [30], and syntheses via Curtius arrangement of cinnamic acids or via an isoquinolone N-oxide have been reported [31].The substitution of the oxygen by nitrogen atom is still one of the most important methods. A number of reagents have been used including ammonia, ammonium acetate, or amines, but the results are never satisfactory [32-34] except for a recently reported method [35].

Design, synthesis and docking studies of some novel isocoumarin analogues as antimicrobial agents

“…Molecular docking can be dened as an optimization problem that would describe the "best-t" orientation of a ligand that binds to a particular protein of interest. 13,14 3-Substituted isocoumarins exhibited valuable pharmacological activities; therefore, in continuation of our work, [15][16][17] efforts have been directed towards the synthesis of new isocoumarin analogues as excellent antimicrobial agents. Peptidoglycans are the main constituents of the bacterial cell wall, which imparts the structural strength to the bacterial cell wall and performs different functions as it counteracts the osmotic pressure of the cytoplasm.…”

Using of 3-Arylisocoumarins in 3-Arylisoquinolons Synthesis

“…У хімічній літературі є хоча й нечисленні, але продуктивні методики одержання ізохінолонів за допомогою формаміду (рис. 13) [27] та ацетату амонію в розчині оцтової кислоти (рис. 14) [28]; остання методика може бути рекомендована для сполук із низькою розчинністю.…”