Citation: Xu Jiao, Zhang Lihong, Zhang Meiqi, Liu Xiubo, Ma Wei, Tang Yixin, Wang Daolin. Iodine-Dimethyl sulfoxide Promoted Synthesis of Novel Tetracyclic Thiazolo[3', 2': 2, 3]pyrido[4, 5-d]pyrido[1, 2-a]pyrimidinones[J]. Chinese Journal of Organic Chemistry, ;2019, 39(10): 2808-2812. doi: 10.6023/cjoc201904033 shu

Iodine-Dimethyl sulfoxide Promoted Synthesis of Novel Tetracyclic Thiazolo[3', 2': 2, 3]pyrido[4, 5-d]pyrido[1, 2-a]pyrimidinones

Xu Jiao ^a,b,† ,
Zhang Lihong ^b,† ,
Zhang Meiqi ^b ,
Liu Xiubo ^b ,
Ma Wei ^a,b,, ,
Tang Yixin ^c ,
Wang Daolin ^c,,

a.
State Key Laboratory of Tree Genetics and Breeding, Northeast Forestry University, Harbin 150040
b.
College of Pharmacy, Heilongjiang University of Chinese Medicine, Harbin 150040
c.
College of Chemistry and Chemical Engineering, Bohai University, Jinzhou 121003

Corresponding author: Ma Wei, mawei@hljucm.net Wang Daolin, wangdaolin@sina.com

^†

Received Date: 12 April 2019
Revised Date: 26 May 2019
Available Online: 12 October 2019

Figures(2)

An iodine-dimethyl sulfoxide (I₂-DMSO) promoted efficient method is described for the synthesis of thiazolo-[3', 2':2, 3]pyrido[4, 5-d]pyrido[1, 2-a]pyrimidin-5-ones (5) via Pictet-Spengler cyclization. The key intermediate, 2-(3-amino-5-phenylaminothiazolo-2-yl)-4H-pyrido[1, 2-a]pyrimidin-4-one (3), was readily prepared from 2-chloromethyl-4H-pyrido-[1, 2-a]pyrimidin-4-one (1) and potassium N-phenyl-N'-cyano-imido-thiocarbonate (2) by Thorpe-Ziegler isomerization. The novel synthetic method offers the advantage of mild reaction conditions, operational simplicity and higher yields.
- pyrido[1, 2-a]pyrimidine,
- thiazolopyridine,
- Thorpe-Ziegler isomerization,
- Pictet-Spengler reaction,
- I₂-DMSO
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