Synthesis of Substituted Phthalimides via Ultrasound-Promoted One-Pot Multicomponent Reaction

Abstract

In this work, a novel strategy for the straightforward synthesis of substituted phthalimides is described, which includes base-mediated Michael addition/intramolecular cyclization/[1,5]-H shift/cleavage of CS 2 /aromatization/nucleophilic acyl substitution reaction of 2-(4-oxo-2-thioxothiazolidin-5-ylidene)acetates and α,α-dicyanoolefines under ultrasound (US) irradiation. Some advantages of this method are as follows: having simple operation, easily accessible starting materials, chemoselective cascade process, synthetically useful yields, and green conditions by utilizing US irradiation as a source of energy and using ethanol as solvent.Article pubs.acs.org/joc

Use of Dialkyl Acetylenedicarboxylates in the Multicomponent Synthesis of Heterocyclic Structures

“…[107] The reaction of benzylamine 2, dimethyl acetylendicarboxylate 1 and CS 2 150 in EtOH afforded methyl 2-(3-benzyl-4-oxo-2-thiooxothiazolidin-5-ylidene)acetate A of substituted phthalimides 216/217 through substitution reaction of 2-(4-oxo-2thioxothiazolidin-5-ylidene)acetates and α,α-dicyanoolefines 214/215 in Et 3 N under reflux in ethanol using ultrasound (US) irradiation (Scheme 87). [108] Synthesis of various quinazolinone phosphonate derivatives 219 through the five-component reaction of euparin 218, primary amines 2, isatin and derivatives 126, dialkyl acetylenedicarboxylates 1 and trimethyl phosphite or 71 in the presence of acidic solution of hydrogen peroxide at room temperature under ultrasonic irradiation was reported by Sharafian et al in 2020 (Scheme 88). [109] sponding products in moderate to excellent yields (Scheme 89).…”

“…The reaction of benzylamine 2 , dimethyl acetylendicarboxylate 1 and CS 2 150 in EtOH afforded methyl 2‐(3‐benzyl‐4‐oxo‐2‐thiooxothiazolidin‐5‐ylidene)acetate A of substituted phthalimides 216/217 through substitution reaction of 2‐(4‐oxo‐2‐thioxothiazolidin‐5‐ylidene)acetates and α,α‐dicyanoolefines 214/215 in Et 3 N under reflux in ethanol using ultrasound (US) irradiation (Scheme 87). [108] …”

Ultrasound-promoted synthesis of novel N-arylamino-3,5′-biquinoline derivatives: their applications in live-cell imaging and in vitro anticancer activity evaluation

“…The methyl and cyano functional groups in these compounds provide two potential nucleophilic and electrophilic sites, and these features enhance the reactivity of these starting materials in multicomponent reactions for the synthesis of various heterocyclic systems, e.g., 5,6-dihydroquinolines, 28 chromonyl dienes, 29 and phthalimides. 30 It is known that ultrasonic irradiation, compared to traditional methods, offers a unique method for the activation and acceleration of chemical reactions, since it permits faster and more selective reactions with better yields under milder conditions. 31 Our interest in ultrasoundassisted reactions and our previous work developing the multicomponent syntheses of functionalized heterocyclic compounds 30 led us to design a method for the synthesis of N-arylamino-3,5 0biquinolines via multicomponent domino reactions of a,adicyanoolefines, and 2-chloro-3-formylquinoline derivatives in EtOH catalyzed by Et 3 N under ultrasonic irradiation with good to excellent yields, and a process that is potentially conducive to natural product synthesis.…”

Recent advances in the synthesis of cyclic compounds using α,α-dicyanoolefins as versatile vinylogous nucleophiles

“…Subsequent elimination of CS 2 generates aromatic intermediate 120 , which transforms into the final product through intramolecular ring closure (Scheme 33). 62…”