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Volumn , Issue 19, 2008, Pages 2941-2944

Efficient synthesis of imidazo[2,1-b][1,3]benzothiazoles and 9H-imidazo-[1,2-a][1,3]benzimidazoles under solvent-free conditions

(4) Adib, Mehdi a Sheibani, Esmail a Zhu, Long Guan b Bijanzadeh, Hamid Reza c

a UNIVERSITY OF TEHRAN (Iran)

b ZHEJIANG UNIVERSITY (China)

c TARBIAT MODARES UNIVERSITY (Iran)

Author keywords

9H imidazo 1,2 a 1,3 benzimidazoles; Heterocycles; Imidazo 2,1 b 1,3 benzothiazoles; Imidazoline 2,4,5 trione; Multicomponent reactions; Solvent free synthesis

Indexed keywords

2 AMINOBENZIDAZOLE DERIVATIVE; 2 AMINOBENZOTHIAZOLE DERIVATIVE; 9H IMIDAZO[1,2 A][1,3]BENZIMIDAZOLE DERIVATIVE; BENZALDEHYDE DERIVATIVE; BENZIMIDAZOLE DERIVATIVE; BENZOTHIAZOLE DERIVATIVE; IMIDAZO[2,1 B][1,3]BENZOTHIAZOLE DERIVATIVE; IMIDAZOLINE 2,4,5 TRIONE; IMIDAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; ONE POT SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 57649134978 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-0028-1083623 Document Type: Article

Times cited : (14)

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- Procedure for the Preparation of 2-(4-Methylphenyl)-N3, E)-1-(4-methylphenyl)methylidene] imidazo[2,1-b, 1,3]benzothiazol-3-amine (6a) A mixture of 2-aminobenzothiazole (0.30 g, 2 mmol, 4-methylbenzaldehyde (0.60 g, 5 mmol, and imidazoline-2,4,5-trione (0.34 g, 3 mmol) was stirred at 200°C for 5 min. Then, the reaction mixture was cooled to r.t. and the residue was purified by column chromatography using n-hexane-EtOAc (1:3) as eluent. The solvent was removed and the product was recrystallized from n-hexane- EtOAc (1:1, The product 6a was obtained as yellow crystals; yield 0.70 g (92, relative to 2-aminobenzothiazole, IR (KBr, 1603, 1495, 1479, 1379, 1352, 1315, 1175, 1146, 1109, 820, 748 cm-1. 1H NMR (500.1 MHz, CDCl3, δ, 2.37, 2.45 (2 x s, 6 H, 2 x CH3, 7.19 (d, J, 7.4 Hz, 2 H, 2 x CH, 7.29-7.32 (m, 3 H, 3 x CH, 7.42 dd
- 4 (372.38): C, 70.96; H, 3.79; N, 15.05. Found: C, 71.0; H, 3.8; N, 14.9.

30
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- Selected X-ray Crystailographic Data for Compound 6a C 24H19N3S, monoclinic, space group, P21/n, a, 12.7579 (12) Å, b, 7.5112 (7) Å, c, 21.2243 (20) Å, β, 91.626 (2)°, V, 2033.03 (3) Å3, T, 295 (2) K, Z, 4, Dcalcd, 1.25 g cm-3, μ, 0.173 mm-1, 2245 observed reflections, final R1, 0.079, wR 2, 0.149 and for all data R1, 0.137, wR2, 0.172. CCDC 671151 contains the supplementary crystallographic data for the structure reported in this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif
- 2 = 0.172. CCDC 671151 contains the supplementary crystallographic data for the structure reported in this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.

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