96923-57-8

Upstream product

• 766-96-1 4-bromo-1-ethynylbenzene 
• 615-43-0 2-iodophenylamine 
• 2258-42-6 formyl acetic anhydride 
• 124-38-9 carbon dioxide 
• 1122-91-4 4-bromo-benzaldehyde 
• 97583-88-5 5-Acetyl-2-amino-4-(4-bromo-phenyl)-4,5-dihydro-pyrano[3,2-b]indole-3-carbonitrile 

Downstream Products

• 96923-56-7 3-Amino-1-(4-bromo-phenyl)-9-oxo-9H-pyrrolo[1,2-a]indole-2-carbonitrile 

Relevant academic research and scientific papers

One-Pot Palladium-Catalyzed Carbonylative Sonogashira Coupling using Carbon Dioxide as Carbonyl Source

Carbonylation coupling reaction has emerged as a powerful and versatile strategy for the construction of carbonyl-containing compounds in modern synthetic chemistry over the past years. Carbon dioxide, a renewable one carbon molecule, has become one of the most attractive and promising alternative carbonyl sources due to its highly abundance, nontoxicity and stability in comparison with CO in recent years. However, in most cases, a two-chamber technique was generally necessary to allow the CO-producing and CO-consuming processes to perform successfully because of the complexities and incompatibility of reaction conditions, when carbon dioxide was utilized as carbonyl source. Herein, a practical one-pot protocol using carbon dioxide as the carbonyl source for the palladium-catalyzed carbonylative Sonogashira coupling has been established, providing an expedient and practical route to a wide range of functionalized alkynones and indoxyls under mild reaction conditions. By finding a suitable catalytic system, the method allowed the CO-generating and CO-consuming processes to proceed in one pot, wherein carbon monoxide was generated in situ from the reduction of carbon dioxide in the absence of any fluoride reagents. Simple and safe operation, readily available substrates, good functional group tolerance and mild reaction conditions are the features of the method.

Design, synthesis and characterization of functionalized pyrazole derivatives bearing amide and sulfonamide moieties from aza-aurones

Abstract: In this work, we report the synthesis of new pyrazole derivatives bearing amide and sulfonamide frameworks from aza-aurones. Firstly, the intermediate spiropyrazolines were obtained through a highly regioselective 1,3-dipolar cycloaddition of nitrilimines with aza-aurones. Subsequently, the obtained cycloadducts were subjected to hydrochloric acid in hot ethanol which conducts to 5-(2-aminobenzoyl)-3,4-diaryl-1-phenylpyrazoles. Finally, the target compounds were obtained separately by the action of acetic anhydride, benzoyl chloride and tosyl chloride on the intermediates 2-aminobenzoylpyrazoles, respectively. Structures of all the synthesized compounds were established using IR, 1H NMR and 13C NMR and mass spectroscopy. Graphic Abstract: Synthesis and characterization of novel heterocyclic systems encompassing pyrazole derivatives from aza-aurones are reported. The synthetic routes used in this work are efficient and relevant, involving the 1,3-dipolar cycloaddition and alkylation reactions. The outcomes show that spectroscopic data fit the structure of all synthesized compounds.[Figure not available: see fulltext.]

A general and convenient palladium-catalyzed synthesis of benzylideneindolin-3-ones with formic acid as the CO source

A general and convenient palladium-catalyzed carbonylative synthesis of 2-benzylideneindolin-3-ones from 2-iodoanilines and arylacetylenes has been developed. With formic acid as the CO source and Ac2O as the activator, a variety of 2-benzylideneindolin-3-ones were obtained in good to excellent yields with exceptional functional group tolerance.

NEW METHOD OF SYNTHESIS OF δ-CARBOLINES FROM 3-INDOLINONE VIA PYRANOINDOLES

2-Arylidene-1-acetylindolin-3-ones were obtained from 1-acetylindolin-3-ones and p-substituted benzaldehydes or 4-pyridinecarboxaldehyde, by the action of malonodinitrile, and were converted into 2-amino-4-aryl-5-acetyl-3-cyanopyranoindoles.When heated with an aqueous-alcoholic solution of KOH, the latter compounds transform into 2-alkoxy-4-aryl-3-cyano-δ-carbolines.The possible paths of formation of δ-carbolines and pyranoindoles are discussed.