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Synthesis 2009(10): 1639-1646  
DOI: 10.1055/s-0028-1088052
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

An Efficient and Chemoselective Synthesis of 1,6-Naphthyridines and Pyrano[3,2-c]pyridines under Microwave Irradiation

Zheng-Guo Han, Shu-Jiang Tu*, Bo Jiang, Shu Yan, Xiao-Hong Zhang, Shan-Shan Wu, Wen-Juan Hao, Xu-Dong Cao, Feng Shi, Ge Zhang, Ning Ma
School of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou, Jiangsu 221116, P. R. of China
Fax: +86(516)83500065; e-Mail: laotu2001@263.net;
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Publication History

Received 6 December 2008
Publication Date:
20 April 2009 (online)

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Abstract

A series of 1,6-naphthyridines and pyrano[3,2-c]pyridines were selectively synthesized via microwave-assisted reactions controlled by the nature of the solvent. This has resulted in an efficient and promising synthetic method for constructing the 1,6-naphthyridine and pyrano[3,2-c]pyridine skeletons.

Key words

solvent-dependent chemoselectivity - 1,6-naphthyridines - pyrano[3,2-c]pyridines

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The single-crystal growth was carried out in ethanol at room temperature. X-ray crystallographic analysis was performed with a Siemens SMART CCD and a Siemens P4 diffractometer (graphite monochromator, MoKα radiation, λ = 0.71073 Å). Crystal data for 4i: empirical formula = C25H20N4S2, formula weight = 440.57, crystal dimensions = 0.13 × 0.12 × 0.03 mm, monoclinic, space group P2(1)/n, a = 11.0619(12) Å, b = 11.2598(13) Å, c = 17.5329(19) Å, α = 90, β = 93.6620(10), γ = 90, µ = 0.265 mm-¹, V = 2179.3(4) ų, Z = 4, D c  = 1.343 g/cm³, F(000) = 920, S = 0.808, R 1 = 0.0665, wR 2 = 0.0863.