86539-76-6Relevant articles and documents
Research on nitro-derivatives of biological interest. XXX Methylated 2-nitronaphthofuranes, synthesis and activity against microorganisms
Einhorn,Demerseman,Royer,Cavier
, p. 175 - 180 (2007/10/02)
2-Nitrofuran derivatives methylated on their heterocycle must be prepared after various methods, according to cases. 1-Methyl 2-nitro naphtho [2. 1-b]furan is formed - with a yield of about 35% - by displacing the keton group of 2-acetyl of 2-acetyl 1-methyl naphtho [2. 1-b]furan using nitric acid in acetic acid. 7-Methoxy 1-methyl 2-nitro naphtho [2. 1-b]furan is obtained by treating 7-methoxy 1-methyl naphtho [2. 1-b]furan with a limited quantity of nitric acid in methylene chloride. Yield near to 10%. 3-Methyl 2-nitro naphtho [2. 3-b]furan is only accessible by deshydrogenation of 3-methyl 2-nitro 5.6.7.8-tetrahydro naphtho [2. 3-b]furan - which synthesis was previously described. Finally, 3-methyl 2-nitro naphtho [1. 2-b]furan is elaborated by action of nitric acid in methylene choride on 2-acetyl 3-methyl naphtho [1. 2-b]furan. Approximate yield: 25%. The methyl group added to the 2-nitro-naphthofuran heterocycle enhances the antibacterial and protozoocidal activities when one passes from 2-nitro naphtho [2. 1-b]furan to 1-methyl 2-nitro naphtho [2.1-b]furan. Nevertheless, it strongly decreases the antibacterial activity when one passes from 7-methoxy 2-nitro naphtho [2. 1-b]furan to 7-methoxy 1-methyl 2-nitro naphtho [2. 1-b]furan. The modifications in the activities noticed in the other cases are of less importance.
