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u00a0A.R.N. Vaishnavi,
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nJanuary 7, 2023 at 11:13 am
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nAbstract
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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.
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Keywords Nitroolefins, baylis-hillman adducts, claisen rearrangement, ethoxybenzaldehyde, disulfanylbenzenamine, (phenylallyl) phenol
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References
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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.
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Journal Menu
Editors Overview
jomcct maintains an Editorial Board of practicing researchers from around the world, to ensure manuscripts are handled by editors who are experts in the field of study.
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- By [foreach 286]n
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A.R.N. Vaishnavi
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- Research Scholar,Department of Chemistry, Government Arts College for men, Chennai-35, Nandhanam,Tamil Nadu,India
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Abstract
nThe 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.n
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Keywords: Nitroolefins, baylis-hillman adducts, claisen rearrangement, ethoxybenzaldehyde, disulfanylbenzenamine, (phenylallyl) phenol
n[if 424 equals=”Regular Issue”][This article belongs to Journal of Modern Chemistry & Chemical Technology(jomcct)]
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Full Text
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Browse Figures
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References
n[if 1104 equals=””]
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.
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Journal of Modern Chemistry & Chemical Technology
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| Volume | 13 |
| Issue | 2 |
| Received | August 5, 2022 |
| Accepted | August 16, 2022 |
| Published | August 30, 2022 |
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