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

Authors

  • N. Sivakumar
  • A. R.N. Vaishnavi
  • K. Mohankrishnan
  • A. Senthil

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.

References

Kita, M. Hirayama, Y. Yamagishi, K. Yoneda, K. Fujisawa, R. Kigoshi, H.J. Am. Chem. Soc. 2012; 134. 20314.

(a)Lee,Y.R. Hung T.V. Tetrahedron 2008;64. 7338. (b). Majumdar, K. C.; Taher, A.; Nandi, R.; Tetrahedron. 2012; 68.5693.

Arora, R.B. Mathur C. N. Brit. J. Pharmacol. 1963. 20. 29.

Sardari, S.Mori .Y. Horita K.Micetich R.G.; Nishibe S. Daneshtalab M. Bioorg. Med. Chem. 1999; 7. 1933.

Rajesh, P.M.Natvar P.J.J. Ad. Pharm Ed & Res, 2011; 1.52.

(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.

Appendino G. Cravotto G. Minassi A. Palmisano G. Eur. J. Org. Chem. 2001; 3711.

Appendino G. Cravotto G. Toma L. Annunziata R. Palmisano G.J. Org. Chem.1994;59.5556.

Mahmoud, A.A. Ahmed, A.A. Iinuma, M. Tanaka T. Phytochemistry 1998; 48. 543.

Mulholland D.A. Iourine S.E. Taylor D.A.H. Dean F.M. Phytochemistry 1998; 47. 1641.

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.

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.

Magiatis P.M.S. Skaltsounis A.L. Tillequin F. Koch M. Pierre A. Atassi G. Chem. Pharm. Bull. 1999;47. 611.

(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.

Guz N.R. Lorenz P. Stermitz F.R. Tetrahedron Lett. 2001;42. 6491.

Downloads

Published

2022-08-30

Issue

Vol. 13 No. 2 (2022)

Section

Research Articles

License

Declaration and Copyright Transfer Form

(to be completed by authors)

I/ We, the undersigned author(s) of the submitted manuscript, hereby declare, that the above manuscript which is submitted for publication in the STM Journals(s), is not published already in part or whole (except in the form of abstract) in any journal or magazine for private or public circulation, and, is not under consideration of publication elsewhere.

  • I/We will not withdraw the manuscript after 1 week of submission as I have read the Author Guidelines and will adhere to the guidelines.
  • I/We Author(s ) have niether given nor will give this manuscript elsewhere for publishing after submitting in STM Journal(s).
  • I/ We have read the original version of the manuscript and am/ are responsible for the thought contents embodied in it. The work dealt in the manuscript is my/ our own, and my/ our individual contribution to this work is significant enough to qualify for authorship.
  •  I/We also agree to the authorship of the article in the following order:

Author’s name                                    

 

1. ________________

2. ________________

3. ________________

4. ________________

 

We  Author(s) tick this box and would request you to consider it as our signature as we agree to the terms of this Copyright Notice, which will apply to this submission if and when it is published by this journal.