Untersuchungen an Diazoverbindugen und Aziden, XXIV. Struktur und Reaktivität des Tosylazid‐Adduktes an Malodinitril

Abstract

Tosylazid addiert sich in stark alkalischem Medium an Malodinitril unter der Bildung von 5‐Tosylamino‐1H‐1,2,3‐triazol‐4‐carbonitril (1). Methylierungen mit Dimethylsulfat (zu 2‐4 und 5‐8), die Synthese von 1 aus 12, verschiedene Abbaureaktionen (1→14,1→16 und 1→17) sowie die Umwandlung von 1 in das Diazotriazol 21 stellen die Struktur des Adduktes sicher und schließen ein Triazenisomeres E aus.

Switchable Synthesis of 4,5-Functionalized 1,2,3-Thiadiazoles and 1,2,3-Triazoles from 2-Cyanothioacetamides under Diazo Group Transfer Conditions

“…In turn, 1,2,3-triazoles may be used in materials chemistry, medicine, and in analytical chemistry. Although sulfonamide group is known as a good pharmacophore group many compounds bearing this moiety are found to exhibit interesting biological activities only a few 5-sulfonylamido-1,2,3-triazoles are published …”

“…Although sulfonamide group is known as a good pharmacophore group many compounds bearing this moiety are found to exhibit interesting biological activities 5 only a few 5-sulfonylamido-1,2,3-triazoles are published. 10 There are several powerful methods for the synthesis of 1,2,3-triazoles published in the literature: thermal and metal catalyzed addition of azides to acetylenes; 1,3-dipolar cycloaddition of azides to alkynes; 1b,4 reactions of azides with methylene active carbonyl compounds; 11 reactions of NH-1,2,3-triazoles with electrophiles; intramolecular cyclizations of α-diazoimines; 11 and dipolar cycloaddition reactions of diazo compounds and nitriles. 11b CuAAC reaction is the most effective among them and widely used to the synthesis of various types of 1,2,3-triazole derivatives.…”

Rearrangement of substituted azido-1,2,3-triazolides to (α-diazoalkyl)tetrazolides

“…Literature procedures were applied for the synthesis of 3b, 5a,6 3c, 7a,b 3e,f, 5a 3g 8 and 3j; 9 an attempt to replace the laborious method for 3g 8 with a more convenient one, i.e. These compounds, like the previously reported 4a, 2 were made routinely by successive diazotisation of the appropriate amines 3 and treatment with sodium azide.…”

“…Access to 3 was effected as follows. Literature procedures were applied for the synthesis of 3b, 5a,6 3c, 7a,b 3e,f, 5a 3g 8 and 3j; 9 an attempt to replace the laborious method for 3g 8 with a more convenient one, i.e. by submitting 3j to the Scheme 1 Pinner reaction in methanol, failed because the methyl imidate hydrochloride salt on hydrolysis lost some methyl chloride, thereby producing the respective amide (R = CONH 2 ) which could not be separated from the target compound 3g.…”

5-Mesylamino-2H-1,2,3-triazole-4-carbonitrile monohydrate

“…The final coordinates and thermal parameters for non-hydrogen atoms are given in Table 1, the parameters for the H atoms in Table 2, and the bond distances and angles in Fig. 1 I" Unpublished results, referred to in Stadler et al (1975). sible triazole isomeric structures.…”