Citation: Zong Chaoyang, Gu Huiwen, Zhang Lijie, Jin Yudong, Sun Yaquan. Microwave-Accelerated Dimroth Rearrangement for the Synthesis of Pyrido [2, 3-d]pyrimidin-4-amine Derivatives[J]. Chinese Journal of Organic Chemistry, ;2018, 38(5): 1165-1171. doi: 10.6023/cjoc201711028 shu

Microwave-Accelerated Dimroth Rearrangement for the Synthesis of Pyrido [2, 3-d]pyrimidin-4-amine Derivatives

Zong Chaoyang ^a,b ,
Gu Huiwen ^b ,
Zhang Lijie ^c ,
Jin Yudong ^a ,
Sun Yaquan ^a,b,c,,

a.
School of Pharmacy, Yancheng Teachers University, Yancheng 224007
b.
Institute of Chemical Technology, Nanjing Tech University, Nanjing 210000
c.
Jiangsu Marine Industry Research Institute, Yancheng 224051

Corresponding author: Sun Yaquan, sunyaquan@hotmail.com
Received Date: 19 November 2017
Revised Date: 3 January 2018
Available Online: 10 May 2018
Fund Project: the Jiangsu Prospective Joint Research Project BY2016066-02Project supported by the Jiangsu Prospective Joint Research Project (No. BY2016066-02) and the College Students Innovation Project (No. 201410324014Z)the College Students Innovation Project 201410324014Z

Figures(3)

In this paper, a novel synthetic method for N-(3, 5-dichlorophenyl)pyrido [2, 3-d]pyrimidin-4-amine was reported, which began from 2-aminonicotinonitrile, following condensation, cyclization and then Dimroth rearrangement reaction under microwave irradiation conditions. The over yield was 90%. Employing the same synthetic method, 20 pyrido [2, 3-d]pyrimidin- 4-amine derivatives were synthesized. We also compared microwave irradiation and oil bath heating for synthetizing the target products. The results showed that the method under microwave irradiation for the preparation of pyrido [2, 3-d]pyrimidin- 4-amine was time-saving and high yield. It is expected to become an efficient, gentle and environmentally friendly synthetic method of pyrido [2, 3-d]pyrimidin-4-amine.
- pyrido[2, 3-d]pyrimidin-4-amine,
- Dimroth rearrangement,
- organic synthesis,
- microwave irradiation
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