89770-20-7

Upstream product

• 120-72-9 indole 
• 90-02-8 salicylaldehyde 
• 109-77-3 malononitrile 
• 1677-46-9 4-hydroxy-1-methyl-2(1H)-quinolone 
• 779-84-0 N-phenylsalicylaldimine 

Relevant academic research and scientific papers

Highly efficient enantioselective three-component synthesis of 2-amino-4H-chromenes catalysed by chiral tertiary amine-thioureas

A three-component cascade reaction of salicylaldehyde, malononitrile/ cyanoacetate and nitromethane catalysed by chiral tertiary amino-thioureas was developed, which leads to the production of highly functionalized 2-amino-4H-chromenes in good yields with good to excellent enantioselectivities.

One-pot 'on-solvent' multicomponent protocol for the synthesis of medicinally relevant 4H-pyrano[3,2-c]quinoline scaffold

'One-pot' AcONa-catalyzed transformation of salicylaldehydes, malononitrile and 4-hydroxy-1-methylquinolin-2(1H)-one in the presence of a minimal quantity of EtOH results in fast (3 min) and efficient formation of unknown 2-amino-4-(2-hydroxyaryl)-6-methyl-5-oxo-5,6-dihydro-4H-pyrano[3,2-c]quinoline-3-carbonitriles in 85-98% yields, which are potential pharmaceutical agents for treating disorders responsive to the induction of apoptosis, antiproliferation, or vascular disruption. This efficient 'on-solvent' approach to the 4H-pyrano[3,2-c]quinoline scaffold represents a novel synthetic concept for multicomponent reaction (MCR) strategy and allows to combine the synthetic virtues of conventional MCR with ecological benefits and convenience of facile 'on-solvent' procedure.

Tantalum vs Niobium MCF nanocatalysts in the green synthesis of chromene derivatives

TaMCF silicas modified with alkaline metals can be considered a novel family of highly efficient bifunctional catalysts involved in the synthesis of chromene derivatives, from salicylaldehyde 2 and acetonitrile compounds, under mild conditions, showing enhanced catalytic performance than their NbMCF analogues. The observed reactivity was mainly attributed to the higher basicity of the Me/TaMCF but also the texture of the samples. The Me/TaMCF silicas showed higher Br?nsted basicity than the Nb ones as indicated by the stronger interaction between alkali metals and Ta in the UV–vis and the test reaction experiments. On the other hand, the basicity of Me/TaMCF together the reactivity degree and steric hindrance of the starting acetonitriles are key factors influencing the reaction selectivity. In conclusion, the basicity of the samples plays an important role initiating the reaction by activation of nucleophile but also a compromise between alkaline cation size and basicity is required.

Facile construction of 3-indolochromenes and 3-indoloxanthenes via EDDF catalyzed one-pot three component reactions

A novel and green strategy for the construction of biologically relevant 3-indolochromene and 3-indoloxanthene scaffolds is reported using EDDF as a catalyst and ethylene glycol as a promoter solvent. The catalytic system offers wider applicability, crossing over a variety of substrates, besides affording exclusively the desired product in shorter reaction times and high yields. Furthermore, the ease of work-up and purification combined with the recyclability of the EDDF-ethylene glycol system makes the present method environmentally sustainable and amenable to large-scale synthesis as well.

Expeditious assembly of a 2-Amino-4H-chromene skeleton by using an enantioselective Mannich intramolecular ring cyclization-tautomerization cascade sequence

Easy to assemble! An enantioselective cascade Mannich intramolecular ring cyclization-tautomerization reaction of malononitrile with 2-hydroxyl N-protected α-amido sulfone is described (see scheme), which provides a new route to the synthesis of the privi