The efficient in‐situ reduction and cyclization reaction of aromatic aldehyde, 1,3‐cyclopentanedione (tetronic acid), and nitro‐compound under SnCl2·2H2O‐THF medium

• Published in: Applied organometallic chemistry Vol. 32; no. 3
• Main Authors: Xu, Hui, Li, Lei, Dai, Lei, Mao, Kaimin, Kou, Wang, Lin, Cong, Rong, Liangce
• Format: Journal Article
• Language: English
• Published: Chichester Wiley Subscription Services, Inc 01.03.2018
• Subjects: Aromatic compounds; Chemical synthesis; Chemistry; in‐situ reduction; pyrazolo[3,2‐f]quinoline; pyrazolo[3,4‐f]quinoline; pyrazolo[4,3‐f]quinoline; Quinoline; Reagents; Reduction; SnCl2·2H2O; Tin chloride
• ISSN: 0268-2605; 1099-0739
• DOI: 10.1002/aoc.4194

An efficient in‐situ reduction and cyclization reaction for the synthesis of pyrazolo[4,3‐f]quinoline, pyrazolo[3,4‐f]quinoline, and pyrazolo[3,2‐f]quinoline derivatives directly form 5‐nitroindazole, 6‐nitroindazole and 5‐nitroindole in the presence of SnCl2·2H2O was reported. Compared to traditional synthetic methods, this approach has the advantages of stable reagents, easy obtaining raw material, and high yields. In this research, SnCl2·2H2O is the efficient reducing agent for the in‐situ reduction and cyclization reaction of nitro‐compound. In addition, this process provided an alternative approach for the synthesis of target compounds. An efficient in‐situ reduction and cyclization reaction for the synthesis of pyrazolo[4,3‐f]quinoline, pyrazolo[3,4‐f]quinoline, and pyrazolo[3,2‐f]quinoline derivatives directly form 5‐nitroindazole, 6‐nitroindazole and 5‐nitroindole under SnCl2·2H2O‐THF medium was reported. Compared to traditional synthetic methods, this approach has the advantages of stable reagents, easy obtaining raw material, and high yields. In this research, SnCl2·2H2O is the efficient reducing agent for the in‐situ reduction and cyclization reaction of nitro‐compound. Moreover, this research provided an alternative approach for the synthesis of target compounds.