Citation: Wang Dao-Lin, Wang Dong, Xing Jin-Juan, Qian Jian-Hua. An efficient method for the synthesis of thieno[3, 2: 2, 3]pyrido[4, 5-d]-thiazolo[3, 2-a] pyrimidinones[J]. Chinese Chemical Letters, ;2017, 28(3): 579-582. doi: 10.1016/j.cclet.2016.11.024 shu

An efficient method for the synthesis of thieno[3, 2: 2, 3]pyrido[4, 5-d]-thiazolo[3, 2-a] pyrimidinones

College of Chemistry and Chemical Engineering, Liaoning Key Laboratory of Synthesis and Application of Functional Compound, Bohai University, Jinzhou 121003, China

Corresponding author: Wang Dao-Lin, wangdaolin@sina.com
Received Date: 19 September 2016
Revised Date: 31 October 2016
Accepted Date: 8 November 2016
Available Online: 24 March 2016

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An efficient method for the preparation of thieno[30, 20:2, 3] pyrido[4, 5-d] thiazolo[3, 2-a] pyrimidin-5-ones 5 is described. The keyintermediate, 7-(3-amino-4-cyano-5-phenylaminothieno-2-yl)-5H-thiazolo-[3, 2-a]pyrimidin-5-one (3), wassynthesizedfrom7-chloromethyl-5H-thiazolo[3, 2-a]pyrimidin-5-one (1) with potassium-(2, 2-dicyano-1-phenylaminoethen-1-yl) thiolate (2) by Thorpe-Ziegler isomerization. Subsequent reaction of the intermediate amine with aromatic aldehydes via Pictet-Spengler reaction provided thieno-pyridine fused thiazolo[3, 2-a] pyrimidines under p-TsOH as catalyst in good yields.
- Thiazolo[3, 2-a]pyrimidinone,
- Thienopyridothiazolo[3, 2-a]pyrimidinone,
- Thorpe-Ziegler isomerization,
- Pictet-Spengler reaction
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