Synthesis and Crystal Structure of 7,8,9,10-Tetrahydro-2-bromo-cyclohepta[ b ]indol-6(5 H )-one
- PDF / 611,016 Bytes
- 5 Pages / 612 x 792 pts (letter) Page_size
- 94 Downloads / 190 Views
TRUCTURE OF ORGANIC COMPOUNDS
Synthesis and Crystal Structure of 7,8,9,10-Tetrahydro-2-bromo-cyclohepta[b]indol-6(5H)-one1 A. Amuthavalli, D. Edison, B. Prakash, M. S. Sivaramkumar, and R. Velmurgan* Department of Chemistry, Kongunadu Arts and Science College, Coimbatore 641029, Tamil Nadu, India *e-mail: [email protected] Received September 14, 2015
Abstract—The title compound, C13H12BrNO, was synthesized and characterised by IR, 1H and 13C NMR spectroscopy. The proposed structure was confirmed by single crystal X-ray diffraction. The single crystal data revealed that the compound crystallizes in the triclinic system, sp. gr. P 1 , with Z = 2. The sevenmembered ring exhibits a slightly distorted envelope conformation. N–H···O hydrogen bonds form a centrosymmetric dimer, these interactions create a stair-like chain of molecules that interacts only loosely with neighbouring chains via van der Waals interactions, and C–H···π contacts are found in the crystal structure. DOI: 10.1134/S1063774517070033
INTRODUCTION Heterocyclic chemistry is one of the most valuable sources of novel compounds with diverse biological activity [1–4]. Indoles and indolines are considered to be privileged structures due to their widespread occurrence in Nature with intricate structural diversity often associated with impressive bioactivities, and in a pharmaceutical sense due to their drug-like properties [5–10]. Seven-membered rings fused with an indole block (cyclohepta[b]indole), containing 5,6,7-tricyclic skeletons, are widely featured in diverse bioactive natural products such as silicine, ervatamine, actinophyllic acid and in numerous pharmaceutical products with diverse activities such as an SIRT1 inhibitor and antitubercular agent [11–15]. Consequently, cyclohepta[b]indoles have received much attention from the synthetic endeavours. Against this background and to ascertain the molecular structure and conformation, the X-ray structure determination of the title compound has been carried out.
(5 mL) was refluxed on an oil bath pre-heated up to 398–403 K for 2 h (Fig. 1). The contents were then cooled and poured onto cold water with stirring. The brown solid which was separated by passing through a column of silica gel and eluted with (95:5, v/v) petroleum ether-ethyl acetate mixture yielded the title compound (0.163 g, 70%). M.p.: 178°C. The crystals of the title compound suitable for single crystal X-ray diffraction (XRD) analysis were obtained by the slow evaporation method by using methylene chloride as solvent at room temperature. Spectroscopic Studies Melting points (Mp) were determined using a Raaga melting point apparatus in capillaries and were uncorrected. FT-IR (KBr, cm–1) spectra were recorded on a Shimadzu spectrophotometer in the region of 500–4000 cm–1. 1H and 13C NMR spectra were recorded on a Bruker (300 and 75 MHz) spectrometer using TMS as an internal reference in CDCl3 (Chemical shifts in δ ppm). Single crystal XRD data
EXPERIMENTAL Synthesis and Crystal Growth of 7,8,9,10-Tetrahydro-2bromo-cyclohepta[
Data Loading...
