Synthesis of Fused Tetrazole Derivatives via a Tandem Cycloaddition and N-Allylation Reaction and Parallel Synthesis of Fused Tetrazole Amines was written by Ek, Fredrik;Manner, Sophie;Wistrand, Lars-Goeran;Frejd, Torbjoern. And the article was included in Journal of Organic Chemistry in 2004.Electric Literature of C8H5F3N2 This article mentions the following:
A method for the synthesis of novel fused tricyclic tetrazoles from allylic bromides generated by the recently discovered DiazAll reaction has been developed. This new tandem reaction comprises a cycloaddition between a nitrile and (TMS)N3 followed by an intramol. N-allylation. The variation of functionalities in the benzene moiety was well-tolerated, and only a moderate difference in yield and degree of purity was noticed. An exo-methylene group in these new compounds permitted further derivatization. Structural resemblance with substances which possess important pharmacol. properties (e.g., losartan and flumazenil) motivated the synthesis of a series of ketones and a small library of amines. A comparison was made between the pharmacophore of (-)-epibatidine and a low energy conformation of N-methyl-5H-tetrazolo[5,1-a][2]benzazepin-6-amine. The reaction of 2-aminobenzonitrile derivatives with 3-bromo-2-(bromomethyl)-1-propene in the presence of tert-Bu nitrite gave 2-[2-(Bromomethyl)-2-propenyl]benzonitrile derivatives I (R = 5-Cl, 5-Br, 4-NO2, 5-NO2, 4-CF3, 4-Cl-5-Br). Treatment of I with (azido)trimethylsilane in the presence of dibutyltin oxide and sequential ozonization gave 5H-tetrazolo[5,1-a][2]benzazepin-6-ones II (same R). Further reductive amination of II gave tetrazolo[5,1-a][2]benzazepin-6-amines III (same R, R1 = H, PhCH2; R1R1N = morpholino, etc.). In the experiment, the researchers used many compounds, for example, 2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1Electric Literature of C8H5F3N2).
2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1) belongs to nitriles. There has been no report on the microbial biosynthesis of nitriles and the physiological function of such enzymes, nor was it not even known whether aliphatic and aromatic nitriles are biological compounds or just petrochemicals. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Electric Literature of C8H5F3N2
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts