5‐Alkylamino‐1H‐1,2,3‐triazoles by Base‐Mediated Cleavage of Cycloadducts of Azides to Cyclic Ketene N,N‐Acetals.

Abstract

Triazole derivatives R 0280 5-Alkylamino-1H-1,2,3-triazoles by Base-Mediated Cleavage of Cycloadducts of Azides to Cyclic Ketene N,N-Acetals. -(QUAST*, H.; ACH, M.; HERGENROETHER, T.; REGNAT, D.; Synthesis 2006, 12, 1943-1945; Inst. Org. Chem., Julius-Maximilians-Univ., D-97074 Wuerzburg, Germany; Eng.) -Klein 42-125

Triazaspirocycles: Occurrence, Synthesis, and Applications

“…Construction of triazaspirocycles is also commonly carried out with azides. Numerous examples of azide-derived triazaspirocycles have been reported using methylene-substituted heterocycles (Schemes 10 and 11 ) [63-67]. Nitrile imines, formed from the corresponding hydrazonoyl chlorides, have also been implemented in the synthesis of triazaspirocycles (Scheme 12 ) [67-69].…”

“…A number of triazaspirocyclic systems are highly susceptible to rearrangement or degradation by hydrolysis, particularly when aromatization results in one or more of the products (Scheme 32 ) [19, 57, 59, 63, 74, 84, 93]. Methylation-driven ring cleavage has been observed in N,N’ -substituted tetrazole- and benzimidazole-based triazaspirocycles (Scheme 33 ) [93].…”

“…1,3 Dipolar cycloaddition of azides with methylene imidazolidines, methylene tetrazoles, and methylene pyrimidines [63]. …”