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Volumn 36, Issue 3, 2007, Pages 450-451

Unexpected spiro-benzoquinolines in the reaction of N-(arylidene) naphthalen-2-amine, arylaldehyde, and 1,3-dimethylbarbituric acid in water

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EID: 34047266628 PISSN: 03667022 EISSN: None Source Type: Journal
DOI: 10.1246/cl.2007.450 Document Type: Article

Times cited : (10)

References (13)

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12
- 34047255014
- General procedure for 4 and 5: A suspension of the mixture of 1,3-dimethylbarbituric acid 1 (2 mmol, N-(arylidene)naphthalen-2- amine 2 (2mmol, arylaldehyde (2 mmol, and TEBAC (0.111 g) was stirred in water (10 mL) at 100°C for 10-14h. The powder formed was collected by filtration, and washed with water. The pure compounds were obtained by silica-gel column chromatography with petroleum ether-acetone (3:1, For the representative compounds 4a and 5a: mp 198-200°C. IR (KBr, v, cm-1, 3390, 3041, 2958, 1743, 1676, 1622, 1558, 1541, 1516, 1478, 1451, 1407, 1377, 1337, 1248, 1149, 1121, 1075, 1020, 810, 756, 703. MS: m/z, 476 (M, 1, 100, 419 (4, 384 (5, 320 (15, 232 (36, 215 (10, 154 (10, Anal. calcd for C30H25N3O 3: C, 75.77; H, 5.30; N, 8.84, Found: C, 75.81; H, 5.38; N, 8.72, Cis isomer 4a: 1HNMR (DMSO-d6, δ, ppm, 2.63 s
- 1H NMR of the product obtained by silica-gel column chromatography.

13
- 34047267944
- X-ray diffraction analysis for 4a: C30H 25N3O3; M, 475.53, lightyellow block crystals, 0.45 × 0.43 × 0.17 mm3, Orthorhombic, space group Pca21, a, 15.8386(16, b, 8.5314(8, c, 17.3856(18) Å, V, 2349.2(4) Å3 Z, 4, Dcalcd, 1.344 g cm -3. F(000, 1000, μ(Mo Kα, 0.088 mm-1. Intensity data were collected on Rigaku Mercury diffractometer with graphite monochromated Mo Kα radiation (λ, 0.71070 Å) using omega scan mode with 3.35° < δ < 25.35°. 2224 unique reflections were measured and 2152 reflections with 1 > 2σ(I) were used in the refinement. Structure solved by direct methods and expanded using Fourier techniques. The final cycle of full-matrix least-squares technique to R, 0.0374 and wR, 0.0888
- -1. Intensity data were collected on Rigaku Mercury diffractometer with graphite monochromated Mo Kα radiation (λ = 0.71070 Å) using omega scan mode with 3.35° < δ < 25.35°. 2224 unique reflections were measured and 2152 reflections with 1 > 2σ(I) were used in the refinement. Structure solved by direct methods and expanded using Fourier techniques. The final cycle of full-matrix least-squares technique to R = 0.0374 and wR = 0.0888.

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