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Synthesis 2014; 46(15): 2065-2070
DOI: 10.1055/s-0033-1338623
DOI: 10.1055/s-0033-1338623
paper
Detritylation of Protected Tetrazoles by Naphthalene-Catalyzed Lithiation
Further Information
Publication History
Received: 03 March 2014
Accepted after revision: 26 March 2014
Publication Date:
30 April 2014 (online)
Dedicated to the honor of Prof. Francisco Foubelo García
Abstract
Treatment of N-tritylated tetrazoles bearing aliphatic, aromatic, or heteroaromatic substituents (including functionalized ones) with lithium powder and a catalytic amount of naphthalene led to reductive removal of the trityl group to give excellent yields of the corresponding free tetrazoles without decomposition of the tetrazole ring. The detritylation process was successfully extended to several tetrazoles that are components of sartans, an interesting class of drugs. The chemoselectivity between trityl–tetrazole and trityl–amine bond-cleavage reactions was also studied. This method represents an efficient technique for deprotection of tritylated tetrazoles under non-acidic conditions.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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References
- 1 For example, see: Applegate HE, Cimarusti CM, Dolfini JE, Funke PT, Koster WH, Puar MS, Slusarchyk WA, Young MG. J. Org. Chem. 1979; 44: 811
- 2 Srimurugan S, Suresh P, Babu B, Hiriyanna SG, Pati HN. Chem. Pharm. Bull. 2008; 56: 383
- 3a Sheppard RC In Comprehensive Organic Chemistry . Vol. 5. Barton D, Ollis WD. Pergamon; Oxford: 1979: 323
- 3b Kunz H, Waldmann H In Comprehensive Organic Synthesis . Vol. 6. Trost BM, Fleming I. Pergamon; Oxford: 1991: 644
- 3c Greene TW, Wuts PG. M. Protective Groups in Organic Synthesis . 3rd ed. Wiley; New York: 1999: 583
- 4a Bodanszky M, Onetti OA. Peptide Synthesis . Interscience; New York: 1966
- 4b Bodanszky M. Principles of Peptide Synthesis . 2nd ed. Springer; New York: 1993: 88
- 5 For example, see: Sharma SK, Songster MF, Colpitts TL, Hegyes P, Barany G, Castellino FJ. J. Org. Chem. 1993; 58: 4993
- 6 Maltese M. J. Org. Chem. 2001; 66: 7615
- 7 Vedejs E, Klapars A, Warner DL, Weiss AH. J. Org. Chem. 2001; 66: 7542
- 8 Rele S, Nayak SK. Synth. Commun. 2002; 32: 3533
- 9 Chandrasekhar S, Nagendra Babu B, Reddy CR. Tetrahedron Lett. 2003; 44: 2057
- 10a Yus M. Chem. Soc. Rev. 1996; 25: 155
- 10b Ramón DJ, Yus M. Eur. J. Org. Chem. 2000; 225
- 10c Yus M. Synlett 2001; 1197
- 10d Yus M, Ramón DJ. Latv. Kim. Z. 2002; 79
- 10e Ramón DJ, Yus M. Rev. Cubana Quim. 2002; 14: 76
- 10f Yus M In The Chemistry of Organolithium Compounds . Vol. 2. Rappoport Z, Mareck I. Wiley; Chichester: 2004. Chap. 11
- 10g Yus M, Herrera RP, Guijarro A. Tetrahedron Lett. 2001; 42: 3455
- 10h Yus M, Herrera RP, Guijarro A. Chem. Eur. J. 2002; 8: 2574
- 10i Herrera RP, Guijarro A, Yus M. Tetrahedron Lett. 2003; 44: 1309
- 11a Gómez C, Ruiz S, Yus M. Tetrahedron Lett. 1998; 39: 1397
- 11b Gómez C, Ruiz S, Yus M. Tetrahedron 1999; 55: 7017
- 11c Yus M, Gómez C, Candela P. Tetrahedron 2002; 58: 6207
- 12a Guijarro D, Pastor IM, Yus M. Curr. Org. Chem. 2011; 15: 375
- 12b Guijarro D, Pastor IM, Yus M. Curr. Org. Chem. 2011; 15: 2362
- 13a Yus M, Foubelo F. Rev. Heteroat. Chem. 1997; 17: 73
- 13b Yus M, Foubelo F. Targets Heterocycl. Syst. 2002; 6: 136
- 13c Yus M. Pure Appl. Chem. 2003; 75: 1453
- 14a Nájera C, Yus M. Trends Org. Chem. 1991; 2: 155
- 14b Nájera C, Yus M. Recent Res. Dev. Org. Chem. 1997; 1: 67
- 14c Nájera C, Yus M. Curr. Org. Chem. 2003; 7: 867
- 14d Nájera C, Sansano JM, Yus M. Tetrahedron 2003; 59: 9255
- 14e Chinchilla R, Nájera C, Yus M. Chem. Rev. 2004; 104: 2667
- 15a Almena J, Foubelo F, Yus M. J. Org. Chem. 1994; 59: 3210
- 15b Almena J, Foubelo F, Yus M. Tetrahedron 1994; 50: 5775
- 15c Almena J, Foubelo F, Yus M. Tetrahedron 1996; 52: 8545
- 15d Alonso E, Guijarro D, Martínez P, Ramón DJ, Yus M. Tetrahedron 1999; 55: 11027
- 15e Guijarro D, Martínez PJ, Nájera C, Yus M. ARKIVOC 2004; (iv): 5
- 16 Yus M, Behloul C, Guijarro D. Synthesis 2004; 1274
- 17 The formation of orange-red solutions of the trityl radical in THF has been described in the literature. For an example, see: Ashby EC, Goel AB, DePriest RN. J. Org. Chem. 1981; 46: 2429
- 18 Chadwick DJ, Hodgson ST. J. Chem. Soc., Perkin Trans. 1 1983; 93
- 19 With the aim of trying to broaden the substrate scope, we tried to prepare some other tetrazoles functionalized with either ester or amide groups but, unfortunately, all our attempts were unsuccessful.
- 20 Yus M, Martínez P, Guijarro D. Tetrahedron 2001; 57: 10119
- 21 Watson SC, Eastham JF. J. Organomet. Chem. 1967; 9: 165
- 22 Koguro K, Oga T, Mitsui S, Orita R. Synthesis 1998; 910
- 23 Zhang CX, Zheng GJ, Bi FQ, Li YL. Chin. Chem. Lett. 2008; 19: 759
- 24 Wang W.-X, Cai H.-L, Xiong R.-G. Chin. Chem. Lett. 2013; 24: 783
- 25 Rama V, Kanagaraj K, Pitchumani K. J. Org. Chem. 2011; 76: 9090
- 26 Yoneyama H, Usami Y, Komeda S, Harusawa S. Synthesis 2013; 45: 1051
- 27 Brubaker CH. Jr. J. Am. Chem. Soc. 1960; 82: 82
- 28 MS data could not be included because this compound decomposed during MS analysis.
- 29 Meazza G, Paravidino P, Bettarini F, Forgia D, Fornara L. WO 2005030736, 2005 ; Chem. Abstr. 2005, 142, 373843
- 30 Patil DR, Wagh YB, Ingole PG, Singh K, Dalal DS. New J. Chem. 2013; 37: 3261
- 31 Sánchez AI, Martínez-Barrasa V, Burgos C, Vaquero JJ, Álvarez-Builla J, Terricabras E, Segarra V. Bioorg. Med. Chem. 2013; 21: 2370
- 32 Ries U, Narr B, Hauel N, Wienen W, van Meel J, Entzeroth M. DE 4142366, 1993 ; Chem. Abstr. 1993, 119, 271155
For reviews, see:
For mechanistic studies, see:
For a polymer-supported version of this reaction, see:
For reviews, see:
For reviews, see:
For reviews, see: