Convenient synthesis of 1-thiohydroxypyrene by Newman-Kwart rearrangement

Abstract

1-Thiohydroxypyrene(1) and its two intermediates, 1-pyrenyl-O-thiocarbamate(2) and 1-pyrenyl-S-thiocarbamate(3), were synthesized using 1-hydroxypyrene as the starting material. The key synthetic step is Newman-Kwart rearrangement. The results indicate that the Newman-Kwart rearrangement is more effective in suitable solvent than conventional method based on pure organic compound. The structures of compounds 1–3 were characterized by FTIR, NMR, GC-MS and elementary analysis. The crystal structures of two new compounds(2 and 3) were determined by single crystal X-ray diffraction analysis. The whole synthetic process is simple, mild and with high yield.

Keywords

Newman-Kwart rearrangement / 1-Thiohydroxypyrene / Crystal structure

References

[1] Coyle J D. Chem. Soc. Rev., 1975, 523.

[2] Bin J K, Yang J H, Hong J I. J. Mater. Chem., 2012, 22(40): 21720.

[3] Zhang L F, Ni Z H, Li D Y, Qin Z H, Wei X Y. Chin. Chem. Lett., 2012, 23(4): 281.

[4] Hyatt J A, Dycus M, Nguyen C, Little J L. Org. Prep. Proced. Int., 2012, 44(3): 256.

[5] Yi J, Fu Y, Xiao B, Cui W C, Guo Q X. Tetrahedron Lett., 2011, 52(2): 205.

[6] Springer D M, Luh B Y, Goodrich J, Bronson J J. Bioorg. Med. Chem., 2003, 11(2): 265.

[7] Collin X, Sauleau A, Bioorg J C. Med. Chem. Lett., 2003, 13(15): 2601.

[8] Štandeker S, Veronovski A, Novak Z, Knez Desalination, 2011, 269(1–3): 223.

[9] Qin W, Xu S M, Xie Q. Int. J. Min. Sci. Technol., 2013, 23(4): 619.

[10] Huang W, Masuda G, Maeda S, Tanaka H, Hino T, Ogawa T. Inorg. Chem., 2008, 47(2): 468.

[11] Kouroulis K N, Hadjikakou S K, Kourkoumelis N, Kubicki M, Male L, Hursthouse M, Skoulika S, Metsios A K, Tyurin V Y, Dolganov A V, Milaeva E R, Hadjiliadis N. Dalton Trans., 2009, 10446.

[12] Hayer A, Halleux V D, Köhler A, El-Garoughy A, Meijer E W. J. Phys. Chem. B, 2006, 110(15): 7653.

[13] Figueira-Duarte T M, Müllen K. Chem. Rev., 2011, 111(11): 7260.

[14] Tong D Y, Duan H F, Wang J J, Zhang L, Cao J G, Wei Z L, Lin Y J. Chem. Res. Chinese Universities, 2014, 30(1): 4.

[15] Painter G F, Smith R J. Tetrahedron, 1997, 53(17): 6073.

[16] Lloyd-Jones G C, Moseley J D, Renny J S. Synthesis, 2008, 661.

[17] Harvey J N, Jover J, Lloyd-Jones G C, Moseley J D, Murray P, Renny J S. Angew. Chem., 2009, 121(41): 7748.

[18] Moseley J D, Sankey R F, Tang O N, Gilday J P. Tetrahedron, 2006, 62(19): 4685.

[19] McManus G J, Perry I J J, Perry M, Wagner B D, Zaworotko M J. J. Am. Chem. Soc., 2007, 129(29): 9094.

[20] Powers D H, Tarbell D S. J. Am. Chem. Soc., 1956, 78(1): 70.

[21] Cristiano Z, Ottorino D L, Raffaella V, Livius C. Top. Curr. Chem., 2007, 131.