Fused thia-heterocycles via isothiocyanates. Part II. A convenient synthesis of some new thieno[2,3-b]thiopyran-4-one derivatives
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Lana Z. El-Agha
,
Marwan R. Kamal
Abstract
A facile synthesis of some methyl 5-(arylamino)-4-oxothieno[2,3-b]thiopyran-6-carboxylates 6a–g is achieved via direct reaction of deprotonated methyl 3-(2,5-dichlorothien-3-yl)-3-oxopropanoate with aryl isothiocyanates in anhydrous tetrahydrofuran (THF) under reflux. Upon saponification of 6a,b, the ester group is eliminated, most logically via decarboxylation of the presumably-formed carboxyl group. Structures of the new compounds 6a–g and 7a,b are supported by microanalytical and spectral [NMR, MS electron impact (EI) and HRMS] data.
References
[1] J. C. Sircar, S. J. Kesten, H. Zinnes, U. S. Patent, 1978, 4, 092, 325; Chem. Abstr.1978, 89, 146889f.Suche in Google Scholar
[2] G. S. Ponticello, M. B. Freedman, C. N. Habecker, M. K. Holloway, J. S. Amato, R. S. Conn, J. J. Baldwin, J. Med. Chem.1987, 30, 591.10.1021/jm00387a002Suche in Google Scholar PubMed
[3] J. J. Baldwin, G. S. Ponticello, P. S. Anderson, M. E. Christy, M. A. Murcko, W. C. Randall, H. Schwam, M. F. Sugrue, J. P. Springer, P. Gautheron, J. Grove, P. Mallorga, M.-P. Viader, B. M. Mckeever, M. A. Navia, J. Med. Chem.1989, 32, 2510.10.1021/jm00132a003Suche in Google Scholar PubMed
[4] I. Shinkai, J. Heterocycl. Chem.1992, 29, 627.10.1002/jhet.5570290304Suche in Google Scholar
[5] T. K. Jones, J. J. Mohan, L. C. Xavier, T. J. Blacklock, D. J. Mathre, P. Sohar, E. T. T. Jones, R. A. Reamer, F. E. Roberts, E. J. J. Grabowski, J. Org. Chem.1991, 56, 763.10.1021/jo00002a050Suche in Google Scholar
[6] T. J. Blacklock, P. Sohar, J. W. Butcher, T. Lamanec, E. J. J. Grabowski, J. Org. Chem.1993, 58, 1672.10.1021/jo00059a013Suche in Google Scholar
[7] L. M. Barhoumi, M. M. El-Abadelah, Salim S. Sabri, W. Voelter, Z. Naturforsch.2017, 72b, 369.10.1515/znb-2016-0271Suche in Google Scholar
[8] G. B. Bachman, L. V. Heisey, J. Am. Chem. Soc.1948, 70, 2378.10.1021/ja01187a019Suche in Google Scholar
[9] M. M. El-Abadelah, M. R. Kamal, W. M. Tokan, S. O. Jarrar, J. Prakt. Chem.1997, 339, 284.10.1002/prac.19973390150Suche in Google Scholar
Supplemental Material:
The online version of this article offers supplementary material (https://doi.org/10.1515/znb-2017-0183).
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Artikel in diesem Heft
- Frontmatter
- In this Issue
- Synthesis and biological evaluation of chalcone-triazole hybrid derivatives as 15-LOX inhibitors
- Synthesis, crystal structure, and photoluminescence of a lithium isothiocyanate compound with 18-crown-6
- Synthesis of madecassic acid derivatives and their cytotoxic activity
- Charge density studies on methylene blue – a potential anti-Alzheimer agent
- Fused thia-heterocycles via isothiocyanates. Part II. A convenient synthesis of some new thieno[2,3-b]thiopyran-4-one derivatives
- Cd(II) and Zn(II) thiocyanate coordination compounds with 3-ethylpyridine: synthesis, crystal structures and properties
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Artikel in diesem Heft
- Frontmatter
- In this Issue
- Synthesis and biological evaluation of chalcone-triazole hybrid derivatives as 15-LOX inhibitors
- Synthesis, crystal structure, and photoluminescence of a lithium isothiocyanate compound with 18-crown-6
- Synthesis of madecassic acid derivatives and their cytotoxic activity
- Charge density studies on methylene blue – a potential anti-Alzheimer agent
- Fused thia-heterocycles via isothiocyanates. Part II. A convenient synthesis of some new thieno[2,3-b]thiopyran-4-one derivatives
- Cd(II) and Zn(II) thiocyanate coordination compounds with 3-ethylpyridine: synthesis, crystal structures and properties
- Aminkomplexe des Goldes, Teil 10: Gold(I)-thiocyanat-Komplexe mit Tetrahydrothiophen, Dimethylsulfid, Ammoniak, Aminen und Azaaromatena
