Zn/MeOH-Mediated Practical and Easy Detritylation of Protected 1-Trityltetrazoles

Dedicated to the memory of Professors Rafael Usón and Tsutomu Katsuki

Abstract

A practical and low-cost method for the detritylation of 1-titryltetrazoles using zinc and methanol is described. This procedure is versatile and efficient in the deprotection of several protected tetrazoles bearing aliphatic, aromatic, and heteroaromatic substituents, as well as some functional groups, without decomposition of the tetrazole ring.

Keywords

tetrazoles - zinc/methanol - detritylation - reductive cleavage

• References

• 1a Erdik E. Organozinc Reagents in Organic Synthesis . CRC Press; Boca Raton: 1996
• 1b Organozinc Reagents: A Practical Approach . Knochel P, Jones P. Oxford University Press; Oxford: 1999
• 2a Knochel P, Singer RD. Chem. Rev. 1993; 93: 2117
• 2b Knochel P, Almena-Perea JJ, Jones P. Tetrahedron 1998; 54: 8275
• 3 See, for instance: Schabel T, Belger C, Plietker B. Org. Lett. 2013; 15: 2858 ; and references therein
• 4a Kocienski P. Protecting Groups, 3rd ed. . Thieme; Stuttgart: 2000
• 4b Wuts PG. M, Greene TW. Protecting Groups in Organic Synthesis, 4th ed. . J. Wiley & Sons; Hoboken: 2007
• 5 Habashi JP, Judge DP, Holm TM, Cohn RD, Loeys BL, Cooper TK, Myers L, Klein EC, Liu G, Calvi C, Podowski M, Neptune ER, Halushka MK, Bedja D, Gabrielson K, Rifkin DB, Carta L, Ramirez F, Huso DL, Dietz HC. Science 2006; 312: 117
• 6 Applegate HE, Cimarusti CM, Dolfini JE, Funke PT, Koster WH, Puar MS, Slusarchyk WA, Young MG. J. Org. Chem. 1979; 44: 811
• 7 Armstrong RW, Moran E. J. Am. Chem. Soc. 1992; 114: 371
• 8a Alsina J, Giralt E, Albericio F. Tetrahedron Lett. 1996; 37: 4195
• 8b Maltese M. J. Org. Chem. 2001; 66: 7915
• 8c Vedejs E, Klapars A, Warner DL, Weiss AH. J. Org. Chem. 2001; 66: 7542
• 8d Vedejs E, Naidu BN, Klapars A, Wagner DL, Li V.-s, Na Y, Holm H. J. Am. Chem. Soc. 2003; 125: 15796
• 9a Zervas L, Theodorpoulos D. J. Am. Chem. Soc. 1956; 78: 1359
• 9b Dugave C, Menez A. J. Org. Chem. 1996; 61: 6067
• 10 Sharma SK, Songster MF, Colpitts TL, Hegyes P, Barany G, Castellino FJ. J. Org. Chem. 1993; 58: 4993
• 11 Chandrasekhar S, Babu BN, Reddy CR. Tetrahedron Lett. 2003; 44: 2057
• 12 Nesvadba H, Roth H. Monatsh. Chem. 1967; 98: 1432
• 13a Behloul C, Guijarro D, Yus M. Synthesis 2004; 1274
• 13b Behloul C, Kenza B, Guijarro D, Nájera C, Yus M. Synthesis 2014; 46: 2065
• 14 Bodansky M, Bednarek MA, Bodansky A. Int. J. Pept. Protein Res. 1982; 20: 387
• 15 Lu RJ, Liu D, Giese RW. Tetrahedron Lett. 2000; 41: 2817
• 16 Behloul C, Bouchemouch K, Guijarro D, Foubelo F, Nájera C, Yus M. Synlett 2015; 26: 2399

See ref. 13a and:
• 17a Yus M, Behloul C, Guijarro D. Synthesis 2003; 2179
• 17b Behloul C, Guijarro D, Yus M. Tetrahedron 2005; 61: 6908
• 17c Behloul C, Guijarro D, Yus M. Tetrahedron 2005; 61: 9319
• 17d Behloul C, Guijarro D, Yus M. Synthesis 2006; 309
• 17e Behloul C, Guijarro D, Yus M. ARKIVOC 2007; (vii): 41
• 17f Behloul C, Chouti A, Guijarro D, Nájera C, Yus M. Synthesis 2015; 47: 507