Thomas, Abraham ; Ila, Hiriyakkanavar ; Junjappa, Hiriyakkanavar (1990) Cyclocondensation of 2-lithiomethylthiazoles and 2-lithiomethylthiazoline with α-oxoketene dithioacetals: synthesis of substituted and annelated thiazolo- and dihydrothiazolo[3,2-a]pyridinium compounds Tetrahedron, 46 (12). pp. 4295-4302. ISSN 0040-4020
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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...
Related URL: http://dx.doi.org/10.1016/S0040-4020(01)86767-3
Abstract
The oxoketene dithioacetals 1 undergo regioselective 1,2-addition with 2-lithiomethyl-4-methylthiazole (2a) and 2-lithiomethylthiazoline (3) to afford the carbinol acetals 4 which on borontrifluoride etherate assisted cyclization yield the corresponding substituted and annelated 3-methyl-5- methylthiothiazolo[3,2-a.] pyridinium tetrafluoroborates (5a- 8, 8a , b, 10, 12) and the dihydro derivatives (23 - 25) respectively in good yields. The corresponding 2-methyl-5-phenylthiazole (16) however underwent both nuclear and side chain deprotonation and yielded a mixture of products under similar reaction conditions.
Item Type: | Article |
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Source: | Copyright of this article belongs to Elsevier Science. |
ID Code: | 24058 |
Deposited On: | 29 Nov 2010 10:31 |
Last Modified: | 22 Feb 2011 05:00 |
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