Borax Catalysed Domino Synthesis of Highly Functionalised Spirooxindole and Chromenopyridine Derivatives: X‐Ray Structure, Hirshfeld Surface Analysis and Molecular Docking Studies

Abstract

Borax efficiently catalysed the synthesis of a series of spirooxindole and chromeno [2, 3-b]pyridine-3-carbonitrile derivatives in domino fashion via Knoevenagel condensation followed by Michael addition. This synthetic scheme is operationally simple, affording excellent yield and can be considered as an approach towards 'green chemistry'. In-silico docking studies of the synthesized molecules were carried to investigate the antitumor activity and to predict its binding affinity and orientation at the active site of human anaplastic lymphoma protein (Protein Data Bank (PDB): 2xp2). Molecular docking studies indicated that 2-amino-5'-chloro-7,7-dimethyl-2',5-dioxo-5,6,7,8-tetrahydrospiro[chromene-4, 3'-indoline]-3-carbonitrile (1 e) and 2 '-amino-5-chloro-2,5'-dioxo-5'H-spiro[indoline-3, 4'pyrano[3, 2-c]chromene]-3'-carbonitrile (2 b) appeared to show strong interactions at the receptor active site with predicted binding energy of À 8.47 kcal/mol and À 9.19 kcal/mol respectively. A detailed analysis of topology of the compounds 1 e and 2 b were also determined by X-ray crystallography and Hirshfeld surface analysis to get an insight of the packing and intermolecular interactions in their molecular structure.

Newly synthesized homomultinuclear Co (II) and Cu (II) bissalamo‐like complexes: Structural characterizations, Hirshfeld analyses, fluorescence and antibacterial properties

“…The light red spot can be expressed as a C–H···O interaction and a Hirshfeld surface. He protrudes from the blue area to represent C···H, H···H and C···C contacts …”

Engaging Isatins in Multicomponent Reactions (MCRs) – Easy Access to Structural Diversity

“…The products were obtained with very good to excellent yields under mild reaction conditions (Scheme 37C). Under these reaction conditions, Borax produces hydroxyl anion (Brønsted base) and boric acid (Lewis acid), which catalyses the Knoevenagel condensation and Michael reactions [68] …”

CsF promoted rapid synthesis of spirooxindole‐pyran annulated heterocycles at room temperature in ethanol

“…These compounds are acknowledged for display of various biological activities like anti‐HIV, antitumor, antitubercular, antimalarial, and central nervous system (CNS) activities and effects . Therefore, different catalysts have been used to synthesize these spirooxindole scaffolds such as alum, l ‐proline, Caspian Isinglass, borax, and gold (III) chloride . Although such protocols reported by others find certain merits of their own.…”