A green and efficient synthetic methodology towards the synthesis of 1-allyl-6-chloro-4-oxo-1,4-dihydroquinoline-3-carboxamide derivatives

BMC Chemistry

Research

Syed Adnan Ali Shah¹  Sharifah Syed Hassan²  Nursyuhada Azzman³  Muhammad Shoaib Ali Gill⁴  Nafees Ahemad⁵ 

[1] Faculty of Pharmacy, Universiti Teknologi MARA Cawangan Selangor Kampus Puncak Alam, 42300, Bandar Puncak Alam, Selangor DE, Malaysia;Jeffrey Cheah School of Medicine and Health Sciences, Monash University Malaysia, Jalan Lagoon Selatan, Bandar Sunway, 47500, Petaling Jaya, Selangor DE, Malaysia;School of Pharmacy, Monash University Malaysia, Jalan Lagoon Selatan, Bandar Sunway, 47500, Petaling Jaya, Selangor DE, Malaysia;Faculty of Pharmacy, Universiti Teknologi MARA, Cawangan Pulau Pinang Kampus Bertam, 13200, Kepala Batas, Pulau Pinang, Malaysia;School of Pharmacy, Monash University Malaysia, Jalan Lagoon Selatan, Bandar Sunway, 47500, Petaling Jaya, Selangor DE, Malaysia;Institute of Pharmaceutical Sciences, University of Veterinary and Animal Sciences, Syed Abdul Qadir Jillani, Out Fall Road, Lahore, Pakistan;School of Pharmacy, Monash University Malaysia, Jalan Lagoon Selatan, Bandar Sunway, 47500, Petaling Jaya, Selangor DE, Malaysia;Tropical Medicine and Biology Multidisciplinary Platform, Monash University Malaysia, Jalan Lagoon Selatan, Bandar Sunway, 47500, Petaling Jaya, Selangor DE, Malaysia;

关键词: Green synthesis;    4-Quinolone;    N-Alkylation;    Carboxamide;    Scalable;   

DOI  :  10.1186/s13065-022-00902-1

 received in 2022-09-02, accepted in 2022-11-14,  发布年份 2022

来源: Springer

【 摘 要 】

Quinolone is a privileged scaffold in medicinal chemistry and 4-Quinolone-3-Carboxamides have been reported to harbor vast therapeutic potential. However, conversion of N-1 substituted 4-Quinolone 3-Carboxylate to its corresponding carbamates is highly restrictive. This motivated us to adopt a much simpler, scalable and efficient methodology for the synthesis of highly pure N-1 substituted 4- Quinolone-3-Carboxamides with excellent yields. Our adopted methodology not only provides a robust pathway for the convenient synthesis of N-1 substituted 4- Quinolone-3-Carboxamides which can then be explored for their therapeutic potential, this may also be adaptable for the derivatization of other such less reactive carboxylate species.

【 授权许可】

CC BY   
© The Author(s) 2022

【 图 表 】

Fig. 7

Fig. 4

Fig. 1

Fig. 1

Fig. 3

Fig. 2

Fig. 8

Fig. 1

Fig. 2

Fig. 5

Fig. 2

Fig. 2

Fig. 2

Fig. 2