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International Letters of Chemistry, Physics and Astronomy
ILCPA Volume 12
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ILCPA > ILCPA Volume 12 > The Chemistry and Synthesis of 1H-indole-2,3-dione...
The Chemistry and Synthesis of 1H-indole-2,3-dione (Isatin) and its Derivatives
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The Chemistry and Synthesis of 1H-indole-2,3-dione (Isatin) and its Derivatives

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Abstract:

Isatins are synthetically versatile substrates, where they can be used for the synthesis of a large variety of heterocyclic compounds. In this, a convenient method has been developed for the conversion of Indoles into Isatins and some heterocyclic derivative were synthesised such as 5- nitro-1H-indole-2,3-dione, 2-methylquinoline-4-carboxylic acid which may be used as raw material for drug synthesis. The general process utilizes the effective method for synthesis of Isatin from Indole is bromination and oxidation with an N-bromosuccinimide-dimethyl sulfoxide reagent. The nitration of Isatin at C-5 takes place by using KNO3, conc. H2SO4, 2-methylquinoline-4-caboxylic acid are usually obtained from pfitzinger reaction.

Info:

Periodical:
International Letters of Chemistry, Physics and Astronomy (Volume 12)
Pages:
30-36
DOI:
https://doi.org/10.18052/www.scipress.com/ILCPA.12.30
Citation:
R. P. Sonawane and R. R. Tripathi, "The Chemistry and Synthesis of 1H-indole-2,3-dione (Isatin) and its Derivatives", International Letters of Chemistry, Physics and Astronomy, Vol. 12, pp. 30-36, 2013
Online since:
April 2013
Authors:
Ratnamala P. Sonawane, Rahul R. Tripathi
Keywords:
2-methylquinoline-4-carboxylic Acid, 5-nitro-1H-indole-2,3-dione, Indole, Isatin, NBS-DMSO, Pfitzinger Reaction
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Open Access

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Creative Commons Attribution 4.0 International License

References:

[1] E. Abele, R. Abele, O. Dzenibs, Chemistry of Hetrocylic Compounds 39 (2003) 1.

[2] E. G. Mesropyan, G. B. Ambrtsumyan, A. A. Avetisyan, Russian Journal Org. Chem. 39(8) (2003) 1130.

[3] M. N. Zemtsova, P. L. Trakhtenborg, Russian Journal Org. Chem. 38 (2003) 1803.

[4] Zh. P. Bespalova, A. E. Lipkin, Khim. -Farm. Zh., 1970, p.24.

[5] R. S. Belen'kaya, A. E. Lipkin,V. M. Ostryakov, Khim. -Farm. Zh., 1972, p.13.

[6] T. Ujiie, Chem. Pharm. Bull. 14 (1966) 461.

[7] W. Pfitzinger, J. Prakt. Chem. 33(2) (1886) 100.

[8] R. Elderfield (editor), Heterocyclic Compounds [in Russian], IL, Moscow 1954, Vol. 3, p.164.

[9] R. Elderfield (editor), Heterocyclic Compounds [in Russian], IL, Moscow 1955, Vol. 4, p.36.

[10] Isatin and its Derivatives [in Russian], Shtiintsa, Kishinev 1977, p.228.

[11] F. D. Popp, Adv. Heterocycl. Chem. 18 (1975) 2.

[12] Joaquime F. M. da Silva, Simon J . Garden, Angelo C. Pinto, Journal of the Brazilian Chemical Society 12(3) (2001) 273-324.

[13] J. Tatsungi, K. Ikuma, Y. Izawa, Tetrahedron Lett. 36 (1995) 8611.

[14] J. Tatsungi, K. Ikuma, Y. Izawa, Heterocycles 43 (1966) 7.

[15] J. Tatsungi, T. Hara, Y. Izawa, Chem. Let. (1977) 177.

[16] J. Xue, Y. Zhang, X-I. Wang, H. K. Fun, J-H. Xu, Org. Lett. 2 (2000) 2538.

[17] V. Nair, K. C. Sheela, N. P. Rath, Chem. Lett. (2000) 980.

[18] D. A. Klumpp, K. Y. Yeung, G. K. S. Prakash, G. A. Olah, J. Org. Chem. 63 (1998) 4481.

[19] P. Hewawasam, M. Erway, Tetrahedron Lett. 39 (1998) 3981.

[20] S. J. Garden, J. C. Torres, A. A. Ferreira, R. B. Silva, A. C. Pinto, Tetrahedron Lett. 38 (1977) 1501.

[22] J. Tatsungi, Y. Izawa, Synth. Commun. 28 (1988) 859.

[23] V. J. Traynelis, W. C. Hergenvother, J. Org. Chem. 29 (1964) 221.

[24] V. J. Traynelis, W. C. Hergenvother, J. Org. Chem. Soc. 86 (1964) 298.

[25] P. G. Gassmen, Jr. B. W. Cue, T-Y. Luth, J. Org. Chem. 42 (1977) 1344.

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Cited By:

[1] Y. Zi, Z. Cai, S. Wang, S. Ji, "Synthesis of Isatins by I2/TBHP Mediated Oxidation of Indoles", Organic Letters, Vol. 16, p. 3094, 2014

DOI: https://doi.org/10.1021/ol501203q

[2] S. Bargavi, S. Gouthaman, M. Sugunnalakshmi, S. Lakshmi, "(R*)-1-Benzyl-3-(2-hydroxyphenyl)indoline-2-one", IUCrData, Vol. 2, 2017

DOI: https://doi.org/10.1107/S2414314617011646

[3] O. Ajani, K. Iyaye, O. Audu, S. Olorunshola, A. Kuye, I. Olanrewaju, "Microwave Assisted Synthesis and Antimicrobial Potential of Quinoline-Based 4-Hydrazide-Hydrazone Derivatives", Journal of Heterocyclic Chemistry, 2017

DOI: https://doi.org/10.1002/jhet.3050

[4] O. Ajani, K. Iyaye, D. Aderohunmu, I. Olanrewaju, M. Germann, S. Olorunshola, B. Bello, "Microwave-assisted synthesis and antibacterial propensity of N ′-s-benzylidene-2-propylquinoline-4-carbohydrazide and N ′-((s- 1H -pyrrol-2-yl)methylene)-2-propylquinoline-4-carbohydrazide motifs", Arabian Journal of Chemistry, 2018

DOI: https://doi.org/10.1016/j.arabjc.2018.01.015

[5] M. Dawar , D. Utreja, R. Rani, K. Kaur, "Synthesis and Evaluation of Isatin Derivatives as Antifungal Agents", Letters in Organic Chemistry, Vol. 17, p. 199, 2020

DOI: https://doi.org/10.2174/1570178616666190724120308

[6] S. Ali Syed, A. Bari, M. Aldughaim, M. Rashid, M. Shariare, M. Kazi, "Analysis of a “3-(Naphthalen-1-ylimino)indolin-2-one” Compound and Its Antimicrobial Assessment Using Lipid-Based Self-Nanoemulsifying Formulations", Molecules, Vol. 26, p. 15, 2020

DOI: https://doi.org/10.3390/molecules26010015
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