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

Abstract

1,4,5-Trialkyltetrazolium salts are convenient synthetic equivalents for hypothetical secondary ynamines in cycloaddition reactions to azides. Thus, the tetrazolium salts are converted into alkylaminotriazoles via deprotonation, cycloaddition to azides, and subsequent base-mediated cleavage of the resulting spirocyclic cycloadducts.

amines - azides - cycloaddition - heterocycles - ring opening - spiro compounds

References

1

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2a Finley KT. 1,2,3-Triazoles, Chemistry of Heterocyclic Compounds   Vol. 39:  Montgomery JA. Wiley; New York: 1980.  p.157 

2b Wamhoff H. In Comprehensive Heterocyclic Chemistry   Vol. 5:  Katritzky AR. Pergamon Press; Oxford, UK: 1984.  p.669 

2c Kadaba PK. Stanovnik B. Tiler M. Adv. Heterocycl. Chem.  1984,  37:  212 

2d Dehne H. In Hetarene III/Part 4, Houben-Weyl   4th ed., Vol. E8d:  Schaumann E. Thieme; Stuttgart: 1994.  p.305 

2e Tomé AC. In Hetarenes and Related Ring Systems: Five-Membered Hetarenes with Three or More Heteroatoms, In Science of Synthesis   Vol. 13:  Storr RC. Gilchrist TL. Shinkai I. Thieme; Stuttgart: 2004.  p.415 

2f Krivolapov VP. Shkurko OP. Russ. Chem. Rev.  2005,  74:  339 

3 Albert A. Adv. Heterocycl. Chem.  1986,  40:  129 

4 Quast H. Ach M. Balthasar J. Hergenröther T. Regnat D. Lehmann J. Banert K. Helv. Chim. Acta  2005,  88:  1589 

5 Quast H. Bieber L. Meichsner G. Regnat D. Chem. Ber.  1988,  121:  1285 

6 For a similar base-induced cleavage of an annulated 1H-4,5-dihydrotetrazole ring see: Moderhack D. Bode D.-O. Schomburg D. Chem. Ber.  1993,  126:  129 

7 Regitz M. Himbert G. Liebigs Ann. Chem.  1970,  70 

8 Voitekhovich SV. Gaponik PN. Ivashkevich OA. Russ. Chem. Rev.  2002,  71:  721 

9 Quast H. Hergenröther T. Liebigs Ann. Chem.  1992,  581 

10 Quast H. Meichsner G. Seiferling B. Liebigs Ann. Chem.  1986,  1891 

11a Lieber E. Chao TS. Rao CNR. J. Org. Chem.  1957,  22:  654 

11b 2-Nitrophenyl azide: Smith PAS. Boyer HJ. Org. Synth. Coll. Vol. IV   Wiley; New York: 1963.  p.74 

12 Quast H. Ach M. Kindermann M. Rademacher P. Schindler M. Chem. Ber.  1993,  126:  503 

13 Macdonald TL. Natalie KJ. Prasad G. Sawyer JS. J. Org. Chem.  1986,  51:  1124