El-Sawah, D., Loksha, Y., Elrazaz, E., Abboud, K., Webster, B., Abouzid, K. (2020). Facile one-pot synthesis of thiazol-2(3H)-imine derivatives from α-active methylene ketones.. Archives of Pharmaceutical Sciences Ain Shams University, 4(2), 237-248. doi: 10.21608/aps.2020.47968.1045
Dalia El-Sawah; Yasser Loksha; Eman Elrazaz; Khalil Abboud; Bradley Webster; Khaled Abouzid. "Facile one-pot synthesis of thiazol-2(3H)-imine derivatives from α-active methylene ketones.". Archives of Pharmaceutical Sciences Ain Shams University, 4, 2, 2020, 237-248. doi: 10.21608/aps.2020.47968.1045
El-Sawah, D., Loksha, Y., Elrazaz, E., Abboud, K., Webster, B., Abouzid, K. (2020). 'Facile one-pot synthesis of thiazol-2(3H)-imine derivatives from α-active methylene ketones.', Archives of Pharmaceutical Sciences Ain Shams University, 4(2), pp. 237-248. doi: 10.21608/aps.2020.47968.1045
El-Sawah, D., Loksha, Y., Elrazaz, E., Abboud, K., Webster, B., Abouzid, K. Facile one-pot synthesis of thiazol-2(3H)-imine derivatives from α-active methylene ketones.. Archives of Pharmaceutical Sciences Ain Shams University, 2020; 4(2): 237-248. doi: 10.21608/aps.2020.47968.1045
Facile one-pot synthesis of thiazol-2(3H)-imine derivatives from α-active methylene ketones.
1Department Pharmaceutical Chemistry, Faculty of Pharmacy, Sinai University, Al-Arish, North Sinai, Egypt.
2Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Sinai University, Al-Arish, North Sinai, Egypt.
3Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Ain shams University, Cairo POX 11566, Egypt.
4Department of Chemistry, University of Florida, Gainesville, FL 32611, USA
5Department Pharmaceutical Chemistry, Faculty of Pharmacy, Sadat University in Egypt,
Abstract
A facile and efficient One-pot procedure was achieved for the synthesis of thiazol-2(3H)-imine derivatives through the bromination of some α-active methylene ketones followed by treatment with potassium thiocyanate and condensation with various primary amines in ethanol as one-pot four-step process. The α-active methylene ketones were symmetrical and asymmetrical ketones. The primary amines used were mostly aromatic amines and also benzylamine was used. This proposed method does not require the use of techniques such as extraction and chromatography. Surprisingly, the product from the reaction of 3-thiocyanacetylacetone and benzylamine was elucidated to be N-(3-benzyl-4-hydroxy-4-methylthiazolidin-2-ylidene)acetamide (2) and not the expected compound 1-(3-benzyl-2-imino-4-methyl-2,3-dihydrothiazol-5-yl)ethan-1-one (1),which was proved based on the existence of the methylene and hydroxyl group in the compound.The mechanism of the novel compound 2 was confirmed by subsequent chemical reactions, spectroscopic data and X-ray crystallography.The molecular structure of all newly synthesized thiazol-2(3H)-imine derivatives were elucidated on the basis of spectroscopic dataand elemental analysis.
Top