Synthesis of N-(3,4,10,10a-Tetrahydro-2H-1,9-dioxa-4a-azaphenanthrene- 6-yl)alkyl and Aryl Sulfonamides

V. Rajachandrasekhar; B. George Vineel; S. Venkataiaha; P.K. Dubey

doi:10.14233/ajchem.2014.17017

Issue

Vol. 26 No. 16 (2014): Vol 26 Issue 16

Issue Published : July 28, 2014

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

Synthesis of N-(3,4,10,10a-Tetrahydro-2H-1,9-dioxa-4a-azaphenanthrene- 6-yl)alkyl and Aryl Sulfonamides

https://doi.org/10.14233/ajchem.2014.17017

V. Rajachandrasekhar

CiVentiChem (India) Private Limited, Plot No 72/A, Part 2 Phase-1, IDA Jeedimetla, Hyderabad-500 055, India

B. George Vineel

CiVentiChem (India) Private Limited, Plot No 72/A, Part 2 Phase-1, IDA Jeedimetla, Hyderabad-500 055, India

S. Venkataiaha

Department of Chemistry, Jawaharlal Nehru Technological University Hyderabad, Kukatpally, Hyderabad-500 085, India

P.K. Dubey

Department of Chemistry, Jawaharlal Nehru Technological University Hyderabad, Kukatpally, Hyderabad-500 085, India

Corresponding Author(s) : V. Rajachandrasekhar

shekar.valamoni@gmail.com

Asian Journal of Chemistry, Vol. 26 No. 16 (2014): Vol 26 Issue 16
Article Published : August 4, 2014

Abstract

Commercially available 2-amino-4-nitrophenol (1) was treated with chloroacetyl chloride to obtain 6-nitro-4H-benzo[1,4]oxazine-3,2-one (2). The latter was reacted with ethyl 3-bromopropionate to obtain 3-(6-nitro-3-oxo-2,3-dihydrobenzo[1,4]oxazine-4-yl)propionic acid ethyl ester (3), which on treatment with lithium aluminiumhydride gave 6-nitro-3,4,10,10a-tetrahydro-2H-1,9-dioxo-4a-azaphenanthrene (4) by reductive cyclization. Compound, 4 was treated with H₂/Pd-C containing di-tert-butyldicarbonate (Boc)₂O in THF to obtain the (3,4,10,10a-tetrahydro-2H-1,9-dioxa-4a-azaphenanthrene-6-yl)carbamic acid tert-butyl ester (5). The latter, on treatment with alkyl or arylsulfonyl chlorides in the presence of NaH gave N-(3,4,10,10a-tetrahydro-2H-1,9-dioxa-4a-azaphenanthrene-6-yl) alkyl or aryl sulfonamide-N¹-carbamic acid tert-butyl ester (6). N-Boc group of 6 was de-protected with Cs₂CO₃/imidazole in acetonitrile to give the title compounds N-(3,4,10,10a-tetrahydro-2H-1,9-dioxa-4a-azaphenanthrene-6-yl) alkyl or aryl sulfonamides (7) as potential anti-bacterial agents. All the new products obtained in the above sequences of reactions have been adequately characterized by spectral data.

Keywords

Synthesis Substituted azaphenanthrenes Reductive cyclization

Rajachandrasekhar, V., George Vineel, B., Venkataiaha, S., & Dubey, P. (2014). Synthesis of N-(3,4,10,10a-Tetrahydro-2H-1,9-dioxa-4a-azaphenanthrene- 6-yl)alkyl and Aryl Sulfonamides. Asian Journal of Chemistry, 26(16), 5263–5267. https://doi.org/10.14233/ajchem.2014.17017

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References

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References

S. Wahindulla and J.J. Bhattacharjee, J. Indian Inst. Sci., 4, 485 (2001).

Y. Katsura, S. Nishino and H. Takasugi, Chem. Pharm. Bull. (Tokyo), 1, 2937 (1991); doi:10.1248/cpb.39.2937.

A.R. Katritzky, M. Pacureanu, S. Slavov, D.A. Dobchev and M. Karelson, Bioorg. Med. Chem., 14, 7490 (2006); doi:10.1016/j.bmc.2006.07.022.

M. Kajino, Y. Shibouta, K. Nishikawa and K. Meguro, Chem. Pharm. Bull. (Tokyo), 39, 2896 (1991); doi:10.1248/cpb.39.2896.

R. Fringuelli, D. Pietrella, F. Schiaffella, A. Garraci, S. Perito, F. Bistoni and A. Vecchiarelli, Bioorg. Med. Chem., 10, 1681 (2002); doi:10.1016/S0968-0896(02)00038-X.

S. Alper-Hayta, E. Aki-Sener, B. Tekiner-Gulbas, I. Yildiz, O. Temiz-Arpaci, I. Yalcin and N. Altanlar, Eur. J. Med. Chem., 41, 1398 (2006); doi:10.1016/j.ejmech.2006.06.011.

S. Deswal and N. Roy, Eur. J. Med. Chem., 41, 552 (2006); doi:10.1016/j.ejmech.2006.01.012.

D. Zhou, B.L. Harrison, U. Shah, H. Andree, G.A. Hornby, R. Scerni, L.E. Schechter, D.L. Smith, K.M. Sullivan and R.E. Mewshaw, Bioorg. Med. Chem. Lett., 16, 1338 (2006); doi:10.1016/j.bmcl.2005.11.054.

M. Ohno, Y. Tanaka, M. Miyamoto, T. Takeda, K. Hoshi, N. Yamada and A. Ohtake, Bioorg. Med. Chem., 14, 2005 (2006); doi:10.1016/j.bmc.2005.10.050.

Z.T. Pio, L.M. Zhao, H.R. Piao and Z.S. Quan, Eur. J. Med. Chem., 43, 1216 (2008); doi:10.1016/j.ejmech.2007.08.006.

Issue

Vol. 26 No. 16 (2014): Vol 26 Issue 16

Synthesis of N-(3,4,10,10a-Tetrahydro-2H-1,9-dioxa-4a-azaphenanthrene- 6-yl)alkyl and Aryl Sulfonamides

Corresponding Author(s) : V. Rajachandrasekhar

Abstract

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