- A new synthesis of 1,3-thiazines and their transformation into 1-substituted-6-alkyluracils by extrusion of carbonyl sulfide
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A simple synthesis of 5-acyl-4-hydroxy-3,6-dihydro-2H-1,3-thiazine-2,6-diones from malonic acid, potassium thiocyanate and acid anhydrides is described. A new, general, regioselective method for the synthesis of 1-substituted-6-alkyluracils by the reaction of these thiazines with primary alkyl and arylamines is reported.
- Yuskovets, Valera N.,Ivin, Boris A.
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- Azines and azoles: CXXII. New regioselective synthesis of 1-substituted 6-alkyluracils
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Readily available 5-acyl-4-hydroxy-3,6-dihydro-2H-1,3-thiazine-2,6-diones with primary alkyl- and arylamines in mild conditions (boiling in propan-2-ol) to give Schiff bases. In more rigid conditions (boiling in DMF), the reaction is accompanied by COS liberation and provides 1-substituted 6-alkyluracils. This previously unknown reaction possesses a considerable synthetic potential and can be considered as a new, general, and regioselective synthetic approach to 1-substituted 6-alkyluracils.
- Yuskovets,Moskvin,Mikhailov,Ivin
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- NOVEL HETEROARYL AND HETEROCYCLE COMPOUNDS, COMPOSITIONS AND METHODS
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The invention relates to novel heteroaryl and heterocycle compounds of formula I and pharmaceutical compositions comprising them, uses and methods thereof for inhibiting the activity of PI3K and for treating inflammatory and autoimmune diseases and cancer.
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Paragraph 223
(2016/08/23)
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- NOVEL HETEROARYL AND HETEROCYCLE COMPOUNDS, COMPOSITIONS AND METHODS
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The invention relates to novel heteroaryl and heterocycle compounds and pharmaceutical compositions comprising them, uses and methods thereof for inhibiting the activity of PI3k and for treating inflammatory and autoimmune disorders diseases and cancer.
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Page/Page column 103; 104
(2014/02/16)
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- NOVEL HETEROARYL AND HETEROCYCLE COMPOUNDS, COMPOSITION AND METHODS THEREOF
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Disclosed are novel heteroaryl and heterocycle compounds of formula I-1, I-2 or I-3 and pharmaceutical compositions comprising them, uses and methods thereof for inhibiting the activity of PI3K and for treating inflammatory and autoimmune diseases and cancer.
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Page/Page column 130; 131
(2014/02/16)
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- NOVEL HETEROARYL AND HETEROCYCLE COMPOUNDS, COMPOSITIONS AND METHODS
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Provided are novel heteroaryl and heterocycle compounds of formula (I-1), (I-2) or (I-3) and pharmaceutical compositions comprising them, uses and methods thereof for inhibiting the activity of PI3K and for treating inflammatory and autoimmune disorders diseases and cancer.
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Page/Page column 132
(2014/02/16)
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- Heterocyclic Transformations. Part 5: Studies in Reactions of 6-Methyl-1,3-oxazine-2,4(3H)-dione with Arylamines - a Facile Synthesis of 1-Aryl-6-methyluracils
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6-Methyl-1,3-oxazine-2,4(3H)-dione 1 reacts with 2 equiv. arylamines 3 at 150-160 deg C to give 1-aryl-6-methyluracils 5 or 1-aryl-3-(3-aryliminobutanoyl)ureas 4.The latter - as well as mixtures of 1 and 3 (2 equiv.) on refluxing, in isopentanol in some cases or in acetic acid in general - provide a facile synthesis of 5.The role of the stoichiometric excess of arylamines as against an equiv. of an alkylamine in similar reactions has been rationalized.
- Singh, Harjit,Singh, Palwinder,Aggarwal, Pawan,Kumar, Subodh
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p. 731 - 736
(2007/10/02)
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