Application of Pfitzinger Reaction in Synthesis of Hetero Ring Annelated Quinoline Carboxylic Acid Derivatives

Taruna Yadav; Neelam K. Yadav; Manju Yadav; Bhawani Singh; D. Kishore

doi:10.14233/ajchem.2016.19532

Issue

Vol. 28 No. 6 (2016): Vol 28 Issue 6

Issue Published : February 29, 2016

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

Application of Pfitzinger Reaction in Synthesis of Hetero Ring Annelated Quinoline Carboxylic Acid Derivatives

https://doi.org/10.14233/ajchem.2016.19532

Taruna Yadav

Department of Chemistry, Banasthali University, Banasthali-304 022, India

Neelam K. Yadav

Department of Chemistry, Banasthali University, Banasthali-304 022, India

Manju Yadav

Department of Chemistry, RPS Degree College, Balana, Mahendergarh-123 029, India

Bhawani Singh

Department of Pure & Applied Chemistry, University of Kota, Kota-324 005, India

D. Kishore

Department of Chemistry, Banasthali University, Banasthali-304 022, India

Corresponding Author(s) : Taruna Yadav

taruna1311@gmail.com

Asian Journal of Chemistry, Vol. 28 No. 6 (2016): Vol 28 Issue 6
Article Published : February 29, 2016

Abstract

The diazotized 8-aminoquinoline (4) was reacted with 2-(hydroxymethylidine)cyclohexanone and N-benzyl 3-(hydroxymethylidine)-piperidine-4-one (5, 6) (generated from the reaction of cyclohexanone and N-benzyl-4-piperidone with ethyl formate in the presence of NaOEt) under the conditions of Japp-Klingemann reaction, followed by Fisher-indolization of the resulting hydrazones in acid, formed the quinolinooxocarbazole (7) and N-benzyl quinolinooxoazacarbazole (8), respectively. Pfitzinger reaction of compounds 7 and 8 with isatin in alkali afforded the corresponding quinoline carboxylic acid derivatives 10 and 11, respectively. In accord to generally accepted mechanism of Pfitzinger reaction, we suggest that the reaction of compounds 7 and 8 with isatin in alkali proceeds with the formation of isatoic acid which undergoes instantaneous cyclocondensation with carbonyl species 7 and 8 to generate compounds 10 and 11, respectively.

Keywords

Quinoline Carbazole Azacarbazole Japp-Klingemann reaction Pfitzinger reaction Quinoline 4-carboxylic acid

Yadav, T., Yadav, N. K., Yadav, M., Singh, B., & Kishore, D. (2016). Application of Pfitzinger Reaction in Synthesis of Hetero Ring Annelated Quinoline Carboxylic Acid Derivatives. Asian Journal of Chemistry, 28(6), 1177–1180. https://doi.org/10.14233/ajchem.2016.19532

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References

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References

A. Caruso, A.S. Voisin-Chiret, J.-C. Lancelot, M.S. Sinicropi, A. Garofalo and S. Rault, Molecules, 13, 1312 (2008); doi:10.3390/molecules13061312.

E.-S.H. El-Ashry and E.-S.I. Ibrahim, Adv. Heterocycl. Chem., 84, 71 (2003); doi:10.1016/S0065-2725(03)84003-5.

S.F. Thakor, D.M. Patel, M.P. Patel and R.G. Patel, Saudi Pharm. J., 15, 48 (2007).

G. Palazzino, L. Cecchi, F. Melani, V. Colotta, G. Filacchioni, C. Martini and A. Lucacchini, J. Med. Chem., 30, 1737 (1987); doi:10.1021/jm00393a009.

M. Sano, Y. Yokoyama, H. Kitani, N. Sakurai, S. Ebara and M. Miyoshi, Chem. Abstr., 133, 135236s (2000).

K. Kubo, Y. Fujwara and T. Isoe, Chem. Abstr., 133, 135235r (2000).

K.J. Raynes, P.A. Stocks, S.A. Ward, P.M. O`Neill and B.K. Park, Chem. Abstr., 133, 193087e (2000).

R.H. Bradbury, G.A. Breault, P.J. Jews Bury and J.E. Pease, Chem. Abstr., 133, 89537r (2000).

C. Ran, L. Xia, P. Ni and J. Fu, Zhongguo Yaoke Doxue Xuebao, 31, 246 (2000); Chem. Abstr., 314, 56548n (2001).

F.I. Carroll, B.D. Berrang and C.P. Linn, J. Med. Chem., 23, 581 (1980); doi:10.1021/jm00179a023.

(a) V.K. Tandon, D.B. Yadav, A.K. Chaturvedi and P.K. Shukla, Bioorg. Med. Chem. Lett., 15, 3288 (2005); doi:10.1016/j.bmcl.2005.04.066; (b) A. Solankee and I. Thakor, Indian J. Chem., 45B, 517 (2006).

I.A. Danish and K.J.R. Prasad, Indian J. Chem., 43B, 1548 (2004).

M.G.A. Shvekhgeimer, Chem. Heterocycl. Compd., 40, 257 (2004); doi:10.1023/B:COHC.0000028623.41308.e5.

H. Pajouhesh, R. Parson and F.D. Popp, J. Pharm. Sci., 72, 318 (1983); doi:10.1002/jps.2600720330.

Issue

Vol. 28 No. 6 (2016): Vol 28 Issue 6

Application of Pfitzinger Reaction in Synthesis of Hetero Ring Annelated Quinoline Carboxylic Acid Derivatives

Corresponding Author(s) : Taruna Yadav

Abstract

Keywords

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