Domino Reaction for the Synthesis of Nitroolefin Heterocyclic Compound Via Thiazole Formation Followed by Claisen Rearrangement

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Year : 2023 | Volume : | : | Page : –
By

A.R.N. Vaishnavi,

  1. Research Scholar Department of Chemistry, Government Arts College for men, Chennai-35, Nandhanam Tamil Nadu India

Abstract

The Baylis-Hillman adducts derived from nitroolefins have been conveniently transformed into Claisen rearrangement. These substances, which include benzothiazole moiety, are very biologically reactive substances. This novel nitro derivative of 2-((E)-2-nitro-3-phenylallyloxy)-3-ethoxybenzaldehyde was simply treated with mole percentage of 2-(2-(2-aminophenyl) disulfanyl) benzenamine in melt reactive condition. Hence this novel 2-(benzo[d]thiazol-2-yl)-6-ethoxy-4-((E)-2-nitro-3-phenylallyl)phenol core unit compounds was very intrusting and new opportunities for the preparation of closely related to the different [3,3] sigmatropic rearrangements related to the Claisen rearrangement molecule. In situ production of a monomer succeeded from an intramolecular [4 + 2] cycloaddition reaction have been shown to be a solid-state melt reaction (SSMR) for the manufacturing of tetracyclic chromenopyran pyrimidinedione frameworks employing Baylis-Hillman derivatives. High stereoselectivity and stereospecificity were used to create the tetracyclic frameworks without the need of a catalyst or solvent. The isolated yield is very good, and the pure product can be obtained without using column chromatography for purification.

Keywords: Nitroolefins, baylis-hillman adducts, claisen rearrangement, ethoxybenzaldehyde, disulfanylbenzenamine, (phenylallyl) phenol

How to cite this article: A.R.N. Vaishnavi. Domino Reaction for the Synthesis of Nitroolefin Heterocyclic Compound Via Thiazole Formation Followed by Claisen Rearrangement. Journal of Modern Chemistry & Chemical Technology. 2023; ():-.
How to cite this URL: A.R.N. Vaishnavi. Domino Reaction for the Synthesis of Nitroolefin Heterocyclic Compound Via Thiazole Formation Followed by Claisen Rearrangement. Journal of Modern Chemistry & Chemical Technology. 2023; ():-. Available from: https://journals.stmjournals.com/jomcct/article=2023/view=89850

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References

1. Kita, M. Hirayama, Y. Yamagishi, K. Yoneda, K. Fujisawa, R. Kigoshi, H.J. Am. Chem. Soc. 2012; 134. 20314.
2. (a)Lee,Y.R. Hung T.V. Tetrahedron 2008;64. 7338. (b). Majumdar, K. C.; Taher, A.; Nandi, R.; Tetrahedron. 2012; 68.5693.
3. Arora, R.B. Mathur C. N. Brit. J. Pharmacol. 1963. 20. 29.
4. Sardari, S.Mori .Y. Horita K.Micetich R.G.; Nishibe S. Daneshtalab M. Bioorg. Med. Chem. 1999; 7. 1933.
5. Rajesh, P.M.Natvar P.J.J. Ad. Pharm Ed & Res, 2011; 1.52.
6. (a) Kashman, Y. Gustafson K.R. Fuller R.W. Cardellina J.H. McMahon J. et al Med. Chem. 1992;35.2735. (b) Lacy A. O’Kennedy, R. Curr. Pharm. Des. 2004;10.3797.
7. Appendino G. Cravotto G. Minassi A. Palmisano G. Eur. J. Org. Chem. 2001; 3711.
8. Appendino G. Cravotto G. Toma L. Annunziata R. Palmisano G.J. Org. Chem.1994;59.5556.
9. Mahmoud, A.A. Ahmed, A.A. Iinuma, M. Tanaka T. Phytochemistry 1998; 48. 543.
10. Mulholland D.A. Iourine S.E. Taylor D.A.H. Dean F.M. Phytochemistry 1998; 47. 1641.
11. Wang Y.Huang S,X.Xia P.Xia Y.Yang Z.Y. Kilgore N. Morris-Natschke S.L. Lee K.H. Bioorg. Med. Chem. Lett. 2007;17. 4316.
12. Elomri A. Michel, S. Skaltsounis A.L. Tillequin F. Koch, M. Pierre A. Guilbaud N. Leonce, S. Kraus L. Rolland Y. Atassi G. J. Med. Chem. 1996; 39.4762.
13. Magiatis P.M.S. Skaltsounis A.L. Tillequin F. Koch M. Pierre A. Atassi G. Chem. Pharm. Bull. 1999;47. 611.
14. (a) Ziegler F.E. Chem. ReV. 1988; 88. 1423. (b) Castro, A.M.M. Chem. ReV. 2004; 104.2939. (c). The Claisen Rearrangement Hiersemann M. Nubbemeyer U. Eds. Wiley-VCH: Weinheim Germany. 2007.
15. Guz N.R. Lorenz P. Stermitz F.R. Tetrahedron Lett. 2001;42. 6491.

Open Access Article
Volume
Received August 5, 2022
Accepted August 16, 2022
Published January 7, 2023
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