Transition metal mediated construction of pyrrole ring on 2,3-dihydroquinolin-4(1H)-one: synthesis and pharmacological evaluation of novel tricyclic heteroarenes

Abstract

A facile two-step method for the construction of fused pyrrole ring leading to 5-substituted 2,3-dihydro-1H-pyrrolo[3,2,1-ij]quinolin-1-ones via C-C followed by intramolecular C-N bond forming reaction is described. In vitro pharmacological evaluation and molecular modelling studies of some of the compounds synthesized are presented.

A Facile Synthesis of Novel Benzofuranyl Benzimidazole Derivatives

“…For the Sonagashira reaction of ( 3 ) with terminal alkyne, many different conditions were explored (Table ).…”

Biomimetic Clauson‐Kass and Paal‐Knorr Pyrrole Synthesis Using β‐Cyclodextrin‐SO3H under Aqueous and Neat Conditions ‐ Application to Formal Synthesis of Polygonatine†

“…Several of its derivatives/natural products show antibacterial, antiviral, anti‐inflammatory, anti‐tumoral, and antioxidant activities (a few illustrated in Figure ). Owing to their importance, a plethora of methods/reactions are available in literature for the synthesis of pyrroles, including the more popular reactions such as Paal–Knorr, Clauson‐Kaas, Hantzsch process, and several other methods such as conjugate addition reactions, transition metal‐mediated reactions, reductive couplings, Aza‐Wittig, as well as multicomponent reactions . Amongst these, Clauson‐Kaas and Paal–Knorr are most commonly used reactions for the synthesis of pyrroles as they use simple and readily available precursors.…”

An Efficient Synthesis of Novel 2‐(5‐indolyl)‐1H‐benzimidazole Derivatives and Evaluation of Their Antimicrobial Activities

“…The synthetic strategy for the target compounds ( 6 ) is shown in Scheme . The synthetic strategy involves the Sonogashira reaction of 4‐(1 H ‐benzimidazol‐2‐yl)‐2‐bromo‐ N , N ‐dimethylaniline ( 3 ) followed by iodocyclization to get novel 2‐(3‐iodo‐5‐indolyl)‐1 H ‐benzimidazole derivatives ( 5 ). The synthetic potential of these new building blocks were demonstrated by palladium‐mediated cross‐coupling reactions which allow diversity‐oriented synthesis at C‐3 position of 2‐(5‐indolyl)‐1 H ‐benzimidazole derivatives.…”