Visible-light-assisted base-catalyzed, one-pot synthesis of highly functionalized cinnolines

Author:

Elkamhawy Ahmed12,Jaragh-Alhadad Laila3,Mekheimer Ramadan Ahmed4,Abdullah Omeima5,Abd-Elmonem Mohamed4,Moustafa Moustafa Sherief3,Abdel-Hameed Afaf4,Mohamed Tahany Mahmoud46,Sadek Kamal Usef4

Affiliation:

1. College of Pharmacy, Dongguk University-Seoul , Goyang , 10326 , Korea

2. Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Mansoura University , Mansoura , 35516 , Egypt

3. Chemistry Department, Faculty of Science, Kuwait University , P.O. Box 12613 , Safat , 13060 , Kuwait

4. Department of Chemistry, Faculty of Science, Minia University , El-Minia 61519 , Egypt

5. Pharmaceutical Chemistry Department, College of Pharmacy, Umm Al‐Qura University , Makkah 21955 , Kingdom of Saudi Arabia

6. Chemotherapy Department, Sohag Cancer Institute , 82511 , Sohag , Egypt

Abstract

Abstract The synthesis of cinnolines has found great interest due to their diverse biological and industrial potency. Yet, the reported synthetic protocols for their synthesis showed limitations that involve harsh reaction conditions such as strong acidic or basic medium, low reaction yields, and using expensive and high loading catalysts. The C–H functionalization has been recognized as intriguing synthetic approach for the synthesis of aromatic/heteroaromatic scaffolds over the past two decades. Here, we reported a novel metal-catalyzed free photocatalytic synthesis of polyfunctionally substituted cinnolines. When ethyl 1-aryl-5-cyano-4-methyl-6-oxo-1,6-dihydropyridazine-3-carboxylates and nitrostyrene derivatives are irradiated with white light (LED 30 W) in ethanol in the presence of piperidine (30 mol%) in open air for 8 h at room temperature, the corresponding polyfunctionally substituted cinnolines are obtained in excellent yields (90–95%) via C–H activation of pyridazine methyl group and nitrostyrene (–N═O) function. Several merits were achieved, which are as follows: (1) the reaction is metal-free; (2) the reaction proceeds with increasing energy efficiency; (3) diversity of functionally substituted cinnolines; (4) high EcoScale value, which reflects the greens of the reaction; and (5) ease handling either in conducting the reaction or in the isolation of products.

Publisher

Walter de Gruyter GmbH

Subject

Health, Toxicology and Mutagenesis,Industrial and Manufacturing Engineering,Fuel Technology,Renewable Energy, Sustainability and the Environment,General Chemical Engineering,Environmental Chemistry

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