Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
Review
. 2010 May 25;15(5):3757-74.
doi: 10.3390/molecules15053757.

Photochemical transformations of tetrazole derivatives: applications in organic synthesis

Luís Miguel Teodoro Frija  1 , Amin Ismael, Maria Lurdes Santos Cristiano
Affiliations
Review

Photochemical transformations of tetrazole derivatives: applications in organic synthesis

Luís Miguel Teodoro Frija et al. Molecules. .

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.

PubMed Disclaimer

Figures

Figure 1
Figure 1
Structures of 1H-tetrazole (1), 1,2,4,5-tetrazine (2), 1H-pentazole (3) and pentazine (4).
Scheme 1
Scheme 1
Photodecomposition of matrix-isolated unsubstituted tetrazole.
Figure 2
Figure 2
Photodecomposition patterns observed for several tetrazole derivatives in criogenic matrices.
Scheme 2
Scheme 2
Photolysis of 8-(p-substituted)tetrazolo[1,5-c]-pyrimidines 10a-d in trifluoro-acetic acid.
Scheme 3
Scheme 3
Synthesis of diaziridinone 16 from photolysis of tetrazolone 15.
Scheme 4
Scheme 4
Synthesis of alkenyl-diaziridinones 18 from photolysis of tetrazolones 17.
Scheme 5
Scheme 5
Synthesis of benzimidazolones 22 from photolysis of tetrazolones 20.
Scheme 6
Scheme 6
Synthesis of carbodiimides 24 from 1,4-disubstituted-1,4-dihydro-1-phenyl-5H-tetrazol-5-thiones 23.
Scheme 7
Scheme 7
Synthesis of iminoaziridines 26a-b by photolysis of alkylidenedihydrotetrazoles 25a-b.
Scheme 8
Scheme 8
Synthesis of iminoaziridine 28 by photolysis of alkylidenedihydrotetrazole 27.
Scheme 9
Scheme 9
Synthesis of iminoaziridines 30 and 31 by photolysis of alkylidene-dihydrotetrazole 29.
Scheme 10
Scheme 10
Synthesis of hexahydronaphthyridine 33 from photolysis of alkylidenedihydrotetrazole 32b.
Scheme 11
Scheme 11
Synthesis of 3,4-dihydro-6-substituted-3-phenylpyrimidin-2(1H)-ones 36a-c from photolysis of 4-allyl-tetrazolones 34a-c.
Figure 3
Figure 3
Stabilisation of pyrimidinone 36a through solvation, in alcoholic solutions.
Scheme 12
Scheme 12
Synthesis of N-phenyl-1,3-oxazines 38a-c from photolysis of 5-allyloxy-1-aryl-tetrazoles 37a-c.
Scheme 13
Scheme 13
Synthesis of iminodiaziridines 40-42 from photolysis of 5-imino-4,5-dihydro-1H-tetrazoles 39.
See this image and copyright information in PMC

References

    1. Bugalho S.C.S., Maçoas E.M.S., Cristiano M.L.S., Fausto R. Low temperature matrix-isolation and solid state vibrational spectra of tetrazole. Phys. Chem. Chem. Phys. 2001;3:3541–3547. doi: 10.1039/b103344c. - DOI
    1. Butler R.N. Comprehensive Heterocyclic Chemistry, II. Pergamon; Oxford, UK: 1996. p. 621.
    1. Butler R.N. Comprehensive Heterocyclic Chemistry, I. Pergamon; New York, NY, USA: 1984. p. 791.
    1. Catalan J., Abboud J.L.M., Elguero J. Basicity and acidity of azoles. Adv. Het. Chem. 1987;41:187–274.
    1. Elguero J., Marzin C., Katritzky A.R., Linda P. The Tautomerism of Heterocycles. Academic Press; New York, NY, USA: 1976. p. 287.

Publication types

MeSH terms

LinkOut - more resources