Diastereoselective synthesis of 1,10-dihydropyrrolo[1,2-a][1,10]phenanthroline derivatives via 1,3-dipolar cycloaddition reaction

Abstract

The functionalized 1,10-dihydropyrrolo[1,2-a][1,10]phenanthroline derivatives were synthesized in good yields and with high diastereoselectivity by 1,3-dipolar cycloaddition reactions of N-phenacylphenanthrolinium bromides or N-ethoxycarbonylmethylene phenanthrolinium bromide with various nitrostyrenes in acetonitrile at room temperature in the presence of triethylamine.

Keywords

Pyridinium ylide / Phenanthroline / Pyrrolo[1,2-a][1,10]phenanthroline / 1,3-Dipolar cycloaddition / Diastereoselectivity

References

[1] Kröhnke F, Zecher W. Angew. Chem. Int. Ed., 1962, 1: 626.

[2] Kröhnke F. Angew. Chem. Int. Ed., 1963, 2: 225.

[3] Yamada S, Yamamoto J, Ohta E. Tetrahedron Lett., 2007, 48: 855.

[4] Kojima S, Hiroikea K, Ohkata K. Tetrahedron Lett., 2004, 45: 3565.

[5] Tsuge O, Kanemasa S, Takenaka S. Bull. Chem. Soc. Jpn., 1985, 58: 3137.

[6] MacGillivray L R, Diamente P R, Reid J L, Ripmeester J A. Chem. Commun., 2000, 359.

[7] Ulrich G, Ziessel R. J. Org. Chem., 2004, 69: 2070.

[8] Eryazici I, Moorefield C N, Durmus S, Newkone G R. J. Org. Chem., 2006, 71: 1009.

[9] Tu S J, Jia R H, Jiang B, Zhang J Y, Zhang Y, Yao C S, Ji S J. Tetrahedron, 2007, 63: 381.

[10] Bora U, Saikia A, Boruah R C. Org. Lett., 2003, 5: 435.

[11] Xia Z Q, Przewloka T, Koya K, Ono M, Chen S J, Sun L J. Tetrahedron Lett., 2006, 47: 8817.

[12] Furdui B, Dinica R, Druta I I, Demeunynck M. Synthesis, 2006, 16: 2640.

[13] Peng W M, Zhu S Z. J. Chem. Soc., Perkin Trans. 1, 2001, 3204.

[14] Hu J X, Jiang X, He T, Zhou J, Hu Y F, Hu H W. J. Chem. Soc., Perkin Trans. 1, 2001, 1820.

[15] Yan C G, Cai X M, Wang Q F, Wang T Y, Zheng M. Org. Biomol. Chem., 2007, 5: 945.

[16] Yan C G, Song X K, Wang Q F, Sun J, Siemeling U, Bruhn C. Chem. Commun., 2008, 1440.

[17] Wang Q F, Song X K, Chen J, Yan C G. J. Comb. Chem., 2009, 11: 1007.

[18] Wang Q F, Hou H, Hui L, Yan C G. J. Org. Chem., 2009, 74: 7403.

[19] Wang Q F, Yan C G. Chem. Res. Chinese Universities, 2009, 25(3): 338.

[20] Wang Q F, Hui L, Hou H, Yan C G. J. Comb. Chem., 2010, 12: 260.

[21] Han Y, Chen J, Hui L, Yan C G. Tetrahedron, 2010, 66: 7743.

[22] Hou H, Zhang Y, Yan C G. Chem. Commun., 2012, 48: 4492.

[23] Hui L, Li H Y, Yan C G. Eur. J. Org. Chem., 2012, 3157.

[24] Wu L, Sun J, Yan C G. Org. Biomol. Chem., 2012, 10: 9452.

[25] Leontie L. Synthetic Metal, 2005, 155: 138.

[26] Nazarenko K G, Shirokaya T I, Shvidenko K V. J. Heterocycl. Compd., 2007, 43: 667.

[27] Dumitrascu F, Caira M R, Barbu L. Revista de Chimie(Bucharest), 2009, 60: 851.

[28] Dueruest Y, Sagirli A, Fronczek F R. Mol. Divers., 2011, 15: 799.

[29] Heydri R, Tahamipour B. Chinese Chem. Lett., 2011, 20: 1281.

[30] Hui L, Yan C G. Tetrahedron, 2011, 67: 2863.

[31] Wu P, Hui L, Gao X, Yan C G. Chem. Res. Chinese Universities, 2012, 28(5): 847.

[32] Muthusaravanan S, Perumal S, Yogeeswari P, Sriram D. Tetrahedron Lett., 2010, 51: 6439.