Facile Synthesis of Octahydroxanthenes by One-Pot Reaction under Solvent-Free Condition

L. Ronibala Devi; L. Vartima Chanu; I. Harimala Chanu; O. Mukherjee Singh

doi:10.14233/ajchem.2016.19746

Issue

Vol. 28 No. 7 (2016): Vol 28 Issue 7

Issue Published : March 31, 2016

This work is licensed under a Creative Commons Attribution 4.0 International License.

Facile Synthesis of Octahydroxanthenes by One-Pot Reaction under Solvent-Free Condition

https://doi.org/10.14233/ajchem.2016.19746

L. Ronibala Devi

Department of Basic Science and Humanities, National Institute of Technology Manipur, Langol-795 004, India

L. Vartima Chanu

Department of Chemistry, Manipur University, Canchipur-795 003, Manipur, India

I. Harimala Chanu

Department of Chemistry, Manipur University, Canchipur-795 003, Manipur, India

O. Mukherjee Singh

Department of Chemistry, Manipur University, Canchipur-795 003, Manipur, India

Corresponding Author(s) : L. Ronibala Devi

laisroni@gmail.com

Asian Journal of Chemistry, Vol. 28 No. 7 (2016): Vol 28 Issue 7
Article Published : March 31, 2016

Abstract

Synthesis of 1,8-dioxo-octahydroxanthenes by cyclocondensation of 5,5-dimethyl-1,3-cyclohexanedione and aromatic aldehydes using catalytic amount of CuCl₂·2H₂O under solvent free condition is reported. Structures of ten compounds are characterized by spectral and analytical data.

Keywords

Tetramethyl-1,8-dioxo-octahydroxanthenes CuCl2·2H2O 5,5-Dimethyl-1,3-cyclohexendione Solvent-free

Devi, L. R., Chanu, L. V., Chanu, I. H., & Singh, O. M. (2016). Facile Synthesis of Octahydroxanthenes by One-Pot Reaction under Solvent-Free Condition. Asian Journal of Chemistry, 28(7), 1528–1530. https://doi.org/10.14233/ajchem.2016.19746

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References

H.K. Wang, S.L. Morris-Natschke and K.-H. Lee, Med. Res. Rev., 17, 367 (1997); doi:10.1002/(SICI)1098-1128(199707)17:4<367::AID-MED3>3.0.CO;2-U.
T. Hideo, Jpn Tokkyo Koho JP (1981); Chem. Abstr., 95, 80922b (1981).
R.W. Lambert, J.A. Martin, J.H. Merrett, K.E.D. Parkes and G.J. Thomas, PCT Int Appl. W09706178 (1997).
J.M. Jamison, K. Krabill, A. Hatwalkar, E. Jamison and C.-c. Tsai, Cell. Biol. Int. Rep., 14, 1075 (1990); doi:10.1016/0309-1651(90)90015-Q.
S. Hatakeyama, N. Ochi, H. Numata and S. Takano, J. Chem. Soc., 1202 (1988); doi:10.1039/c39880001202.
C.N. O'Callaghan, T.B.H. McMurry, J.E. O'Brien and S.M. Draper, J. Chem. Res. (S), 312 (1997); doi:10.1039/A701462G.
G. Pohlers, J.C. Scaiano and R. Sinta, Chem. Mater., 9, 3222 (1997); doi:10.1021/cm970587p.
C.G. Knight and T. Stephens, Biochem. J., 258, 683 (1989); doi:10.1042/bj2580683.
S.A. Hilderbrand and R. Weissleder, Tetrahedron Lett., 48, 4383 (2007); doi:10.1016/j.tetlet.2007.04.088.
(a) K. Nagarajan and S.J. Shenoy, Indian J. Chem., 31B, 73 (1992); (b) H. Ankati, J. Chem. Soc., 4877 (1963); doi:10.1039/JR9630004877.
J.P. Poupelin, G.S. Ruf, O.F. Blandpin, G. Narcisse, G.U. Ernouf and R. Lacroix, Eur. J. Med. Chem., 13, 67 (1978).
D. Fang, K. Gong and Z.-L. Liu, Catal. Lett., 127, 291 (2009); doi:10.1007/s10562-008-9677-0.
G. Song, B. Wang, H. Luo and L. Yang, Catal. Commun., 8, 673 (2007); doi:10.1016/j.catcom.2005.12.018.
(a) T. Mizutani, Y. Ukaji and K. Inomata, Bull. Chem. Soc. Jpn., 76, 1251 (2003); doi:10.1246/bcsj.76.1251; (b) X. Huang, H. Zhou and W. Chen, J. Org. Chem., 69, 839 (2004); doi:10.1021/jo035225h; (c) O.A. Attanasi, P. Filippone, S. Santeusanio and F. Serra-Zanetti, Synthesis, 381 (1987); doi:10.1055/s-1987-27952; (d) M.G. Vinogradov, A.E. Kondorsky and G.I. Nikishin, Synthesis, 60 (1988); doi:10.1055/s-1988-27465.
(a) O.M. Singh, S.J. Singh, M.B. Devi, L.N. Devi, N.I. Singh and S.-G. Lee, Bioorg. Med. Chem. Lett., 18, 6462 (2008); doi:10.1016/j.bmcl.2008.10.063; (b) O.M. Singh and S.J. Singh, Tetrahedron Lett., 49, 3991 (2008); doi:10.1016/j.tetlet.2008.04.093; (c) O.M. Singh, N.S. Devi, L.R. Devi, K.B. Lim, Y.J. Yoon and S.-G. Lee, Bull. Korean Chem. Soc., 32, 175 (2011); doi:10.5012/bkcs.2011.32.1.175.

References

H.K. Wang, S.L. Morris-Natschke and K.-H. Lee, Med. Res. Rev., 17, 367 (1997); doi:10.1002/(SICI)1098-1128(199707)17:4<367::AID-MED3>3.0.CO;2-U.

T. Hideo, Jpn Tokkyo Koho JP (1981); Chem. Abstr., 95, 80922b (1981).

R.W. Lambert, J.A. Martin, J.H. Merrett, K.E.D. Parkes and G.J. Thomas, PCT Int Appl. W09706178 (1997).

J.M. Jamison, K. Krabill, A. Hatwalkar, E. Jamison and C.-c. Tsai, Cell. Biol. Int. Rep., 14, 1075 (1990); doi:10.1016/0309-1651(90)90015-Q.

S. Hatakeyama, N. Ochi, H. Numata and S. Takano, J. Chem. Soc., 1202 (1988); doi:10.1039/c39880001202.

C.N. O'Callaghan, T.B.H. McMurry, J.E. O'Brien and S.M. Draper, J. Chem. Res. (S), 312 (1997); doi:10.1039/A701462G.

G. Pohlers, J.C. Scaiano and R. Sinta, Chem. Mater., 9, 3222 (1997); doi:10.1021/cm970587p.

C.G. Knight and T. Stephens, Biochem. J., 258, 683 (1989); doi:10.1042/bj2580683.

S.A. Hilderbrand and R. Weissleder, Tetrahedron Lett., 48, 4383 (2007); doi:10.1016/j.tetlet.2007.04.088.

(a) K. Nagarajan and S.J. Shenoy, Indian J. Chem., 31B, 73 (1992); (b) H. Ankati, J. Chem. Soc., 4877 (1963); doi:10.1039/JR9630004877.

J.P. Poupelin, G.S. Ruf, O.F. Blandpin, G. Narcisse, G.U. Ernouf and R. Lacroix, Eur. J. Med. Chem., 13, 67 (1978).

D. Fang, K. Gong and Z.-L. Liu, Catal. Lett., 127, 291 (2009); doi:10.1007/s10562-008-9677-0.

G. Song, B. Wang, H. Luo and L. Yang, Catal. Commun., 8, 673 (2007); doi:10.1016/j.catcom.2005.12.018.

(a) T. Mizutani, Y. Ukaji and K. Inomata, Bull. Chem. Soc. Jpn., 76, 1251 (2003); doi:10.1246/bcsj.76.1251; (b) X. Huang, H. Zhou and W. Chen, J. Org. Chem., 69, 839 (2004); doi:10.1021/jo035225h; (c) O.A. Attanasi, P. Filippone, S. Santeusanio and F. Serra-Zanetti, Synthesis, 381 (1987); doi:10.1055/s-1987-27952; (d) M.G. Vinogradov, A.E. Kondorsky and G.I. Nikishin, Synthesis, 60 (1988); doi:10.1055/s-1988-27465.

(a) O.M. Singh, S.J. Singh, M.B. Devi, L.N. Devi, N.I. Singh and S.-G. Lee, Bioorg. Med. Chem. Lett., 18, 6462 (2008); doi:10.1016/j.bmcl.2008.10.063; (b) O.M. Singh and S.J. Singh, Tetrahedron Lett., 49, 3991 (2008); doi:10.1016/j.tetlet.2008.04.093; (c) O.M. Singh, N.S. Devi, L.R. Devi, K.B. Lim, Y.J. Yoon and S.-G. Lee, Bull. Korean Chem. Soc., 32, 175 (2011); doi:10.5012/bkcs.2011.32.1.175.

Issue

Vol. 28 No. 7 (2016): Vol 28 Issue 7

Facile Synthesis of Octahydroxanthenes by One-Pot Reaction under Solvent-Free Condition

Corresponding Author(s) : L. Ronibala Devi

Abstract

Keywords

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