Photochemical Transformations of Tetrazole Derivatives: Applications in Organic Synthesis

Abstract

Abstract:Tetrazoles remain a challenge to photochemists. Photolysis leads to cleavage of the tetrazolyl ring, may involve various photodegradation pathways and may produce a diversity of photoproducts, depending on the structure and conformational flexibility of the substituents and the possibility of tautomerism. If the photochemistry of tetrazoles is considered within the frame of synthetic applications the subject is even more challenging, since the ultimate goal is to achieve selectivity and high yield. In addition, the photoproducts must remain stable and allow isolation or trapping, in order to be used in other reactions. This review summarises the photochemical transformations of tetrazole derivatives that can be used as effective synthetic routes to other compounds.

Sigmatropic rearrangements in 5-allyloxytetrazoles

“…In conclusion, analysis of the 1 H-NMR spectra of the compounds obtained shows that tetrazolones 12 and 15 are the (14). Middle: Structure of the rearrangement product resulting from [3,3¢]-sigmatropic migration of the allylic system: 1-(3,7-dimethylocta-1,6-dien-3-yl)-4-phenyl-1H-tetrazol-5(4H)-one (15). Bottom: Structure of the rearrangement product resulting from [1,3¢]-sigmatropic migration of the allylic system: (E) -1 -(3,7 -dimethylocta -2,6 -dienyl) -4 -phenyl -1H -tetrazol -5(4H)-one (18).…”

“…• C. (15). The solution remaining from the recrystallization of ether 14 was evaporated under reduced pressure, to afford the required product as yellow oil (1.6 g, 36% yield).…”

Green Primary Explosives

“…As such, their major decomposition product is inert and nontoxic N 2 gas. In addition to energetic uses, tetrazoles also have applications in pharmaceuticals and organic synthesis [68].…”

Synthesis of some novel purine derivatives incorporating tetrazole ring and investigation of their antimicrobial activity and DNA interactions

“…These nitrogen-rich compounds are widely used as propellants and explosives (Shelkar et al, 2013). In crop protection they are used as plant growth regulators, herbicides, and fungicides (Shelkar et al, 2013;Frija et al, 2010). However, the most important use of tetrazoles is to be found in medicinal chemistry (Frija et al, 2010).…”