Synthesis, spectroscopic characterization, and crystal structure of a novel indoline derivative
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TRUCTURE OF ORGANIC COMPOUNDS
Synthesis, Spectroscopic Characterization, and Crystal Structure of a Novel Indoline Derivative1 Sakshi Sharmaa, Goutam Brahmacharib, Bubun Banerjeeb, Khondekar Nurjamalb, Rajni Kanta, and Vivek K. Guptaa,* aX-ray
Crystallography Laboratory, Post-Graduate Department of Physics and Electronics, University of Jammu, Jammu Tawi-180006, India b Laboratory of Natural Products and Organic Synthesis, Department of Chemistry, Visva-Bharati (a Central University), Santiniketan-731235, West Bengal, India *e-mail: [email protected] Received November 30, 2015
Abstract—A new indoline derivative, tert-butyl 2'-amino-3'-cyano-6'-methyl-2-oxospiro[indoline-3,4'pyran]-5'-carboxylate is eco-friendly synthesized, and its spectral properties and X-ray crystal structure are studied. In the molecule, the oxindole and pyran moieties are perpendicular to each other. The crystal structure is stabilized by intermolecular N−H···O and intramolecular C−H···O hydrogen bonds. Centrosymmetric dimer units are formed by intermolecular N−H···O hydrogen bonds. In addition, one C−H···π interaction is also observed. DOI: 10.1134/S1063774516070117
INTRODUCTION Spiro-oxindole scaffolds represent a “privileged” structural motif well-distributed in naturally occurring compounds such as spirotryprostatin (A and B), pteropodine, marcfortine B, and glesemine [1]. This unique part-structure is also very common in many synthetic bioactive compounds. Pyran-annulated heterocyclic scaffolds are also very common in naturally occurring compounds [2, 3] with a broad spectrum of significant biological activities [4–7]. Recently, a series of synthetic 2-amino-3-cyano-pyrans have been evaluated to possess potent anticancer [8–11], antibacterial and antifungal [12, 13], and anti-rheumatic [14] properties. In this communication, we wish to report on onepot facile synthesis of a spiro-oxindole fused pyran compound, namely tert-butyl 2'-amino-3'-cyano-6'methyl-2-oxospiro[indoline-3,4'-pyran]-5'-carboxylate via three-component reaction at room temperature using commercially available trisodium citrate dihydrate as inexpensive and environmentally benign organo-catalyst, and its crystal structure. The structure of the title compound was elucidated by spectral methods and XRD studies. EXPERIMENTAL General. Infrared spectra were recorded using a Shimadzu (FT-IR 8400S) FT-IR spectrophotometer 1 The article is published in the original.
using KBr disc. 1H and 13C NMR spectra were obtained at 400 and 100 MHz, respectively, using a Bruker DRX-400 spectrometer and DMSO-d6 as the solvent. Mass spectra (TOF-MS) were measured on a QTOF Micro mass spectrometer. Elemental analyses were performed with an Elementar Vario EL III Carlo Erba 1108 microanalyzer instrument. The melting point was recorded on a Chemiline CL-725 melting point apparatus and is uncorrected. Thin layer chromatography (TLC) was performed using silica gel 60 F254 (Merck) plates. Synthesis. An oven-dried screw cap test tube was charged with a magnetic stir bar, isatin (1; 0.147 g
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