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Volumn , Issue 16, 2007, Pages 2596-2598

A versatile one-pot synthesis of fused polycyclic imidazole-naphthoquinone derivatives through imidazole-4,5-quinodimethane generation followed by Diels-Alder cycloaddition

(3) Neochoritis, Constantinos a Stephanidou Stephanatou, Julia a Tsoleridis, Constantinos A a

a ARISTOTLE UNIVERSITY OF THESSALONIKI (Greece)

Author keywords

Crown ether; Diels Alder reactions; Fused imidazolenaphthoquinones; Imidazole o quinodimethanes; One pot reaction

Indexed keywords

1,4 NAPHTHOQUINONE DERIVATIVE; 2 QUINODIMETHANE DERIVATIVE; ALKANE DERIVATIVE; BROMINE; HYDROGEN; IMIDAZOLE 4,5 QUINODIMETHANE; IMIDAZOLE DERIVATIVE; PHENYLQUINONE; TOLUENE; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; COLUMN CHROMATOGRAPHY; CYCLOADDITION; DIELS ALDER REACTION; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ONE POT SYNTHESIS; STEREOCHEMISTRY;

EID: 35348930015 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-986656 Document Type: Article

Times cited : (3)

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- All melting points were determined on a Büchi apparatus and are uncorrected. The 1H NMR and 13C NMR spectra were recorded on a Bruker AM300 spectrometer in CDCl3 with TMS as internal standard. All coupling constants are given in Hz and chemical shifts are given in ppm. Selected Data for Compound 4: Mp 125-127°C. IR (mull) νmax, 1666, 1604 cm-1. 1H NMR22 (300 MHz, CDCl3, δ, 3.570 (s, 3 H, NMe, 6.418 (m, J, 9.1, 2.6 Hz, 2 H, C-2′, C-6′, 6.982 (d, J, 10.4 Hz, 1 H, C-7 or C-6, 7.014 (d, J, 10.4 Hz, 1 H, C-6 or C-7, 7.365 (m, J, 9.1, 2.6 Hz, 2 H, C-3′, C-5′, 7.900 (d, J, 0.5 Hz, 1 H, C-9, 8.43 (d, J, 0.5 Hz, 1 H, C-4, 13C NMR (75 MHz, CDCl3, δ, 40.3 (NMe, 108.6 (C-9, 114.2 (C-4′, 114.4 (C-2′, C-6′, 116.2 (C-2, 119.6 (C-4, 128.6 (C-8a, 132.6 C-3
- 2 (432.27): C, 61.13; H, 3.26; N 9.72. Found: C, 61.25; H, 3.17; N, 9.65.

37
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- The multiplicities and chemical shifts of the aromatic protons have been confirmed after simulation with program Spin Works, version 2.2.0, available from
- The multiplicities and chemical shifts of the aromatic protons have been confirmed after simulation with program Spin Works, version 2.2.0, available from ftp://davinci.chem.umanitoba.ca.

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