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Synthesis 2018; 50(17): 3430-3435
DOI: 10.1055/s-0037-1610170
DOI: 10.1055/s-0037-1610170
paper
Indium-, Magnesium-, and Zinc-Mediated Debenzylation of Protected 1H-Tetrazoles: A Comparative Study
Authors
This work was financially supported by the Agence National pour le Développement de la Reserch en Santé (Algérie) and the Spanish Ministerio de Ciencia e Innovación (CTQ2011-24155, CTQ2011-24165), the Ministerio de Economía y Competitividad (CTQ2013-43446-P, CTQ2014-51912-REDC, CTQ2014-53695-P, CTQ2017-85093-P), FEDER, the Generalitat Valenciana (PROMETEO 2009/039, PROMETEOII 2014/017), and the University of Alicante. We also thank the Spanish Ministerio de Asuntos Exteriores y de Cooperación (AP/039112/11).
Weitere Informationen
Publikationsverlauf
Received: 31. März 2018
Accepted after revision: 30. April 2018
Publikationsdatum:
25. Juni 2018 (online)
Dedicated to Professor Vicente Gotor on the occasion of his retirement
Abstract
5-Substituted 1-benzyltetrazoles are easily debenzylated to give the corresponding deprotected tetrazoles using dissolved metals under protic conditions: Mg/MeOH, In/MeOH, or Zn/MeCO2H are the procedures of choice for this transformation.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610170.
- Supporting Information (PDF)
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References
- 1 See, for instance: Wuts PG. M. Greene TW. Greene’s Protective Groups in Organic Synthesis . Wiley-Interscience; Hoboken: 2007. 4th ed.
- 2 Babu SN. N. Srinivasa GR. Santhosh DC. Gowda DC. J. Chem. Res. 2004; 66
- 3 Felpin F.-X. Fouquet E. Chem. Eur. J. 2010; 16: 12440
- 4 Sultane PR. Mete TB. Bhat RG. Tetrahedron Lett. 2015; 56: 2067
- 5 Papageorgiou EA. Gaunt MJ. Yu J.-q. Spencer JB. Org. Lett. 2000; 2: 1049
- 6 Tanielyan SK. Alvez G. Marín N. Agustine RL. Top. Catal. 2014; 57: 1359
- 7 Popova EA. Protas AV. Trifonov RE. Anticancer Agent Med. Chem. 2017; 17: 1856
- 8a Yus M. Behloul C. Guijarro D. Synthesis 2003; 2179
- 8b Behloul C. Guijarro D. Yus M. Synthesis 2004; 1274
- 8c Behloul C. Bouchelouche K. Guijarro D. Nájera C. Yus M. Synthesis 2014; 46: 2065
- 8d Behloul C. Bouchelouche K. Guijarro D. Foubelo F. Nájera C. Yus M. Synlett 2015; 26: 2399
- 8e Behloul C. Bouchelouche K. Hadji Y. Benseghir S. Guijarro D. Nájera C. Yus M. Synthesis 2016; 48: 2455
- 8f Behloul C. Chouti A. Guijarro D. Foubelo F. Nájera C. Yus M. Tetrahedron 2016; 72: 7937
- 8g Behloul C. Chouti A. Chabour I. Bey HB. Guijarro D. Foubelo F. Nájera C. Yus M. Tetrahedron Lett. 2016; 57: 3526
- 9 Behloul C. Chouti A. Guijarro D. Nájera C. Yus M. Synthesis 2015; 47: 507
- 10 Behloul C. Guijarro D. Yus M. Synthesis 2006; 309
- 11 Behloul C. Guijarro D. Yus M. Tetrahedron 2005; 61: 6908
- 12 Behloul C. Guijarro D. Yus M. Tetrahedron 2005; 61: 9319
- 13 Almansa R. Behloul C. Guijarro D. Yus M. ARKIVOC 2007; (vii): 41
- 14 Koguro K. Oga T. Mitsui S. Orita R. Synthesis 1998; 910
- 15 Tisseh ZN. Dabiri M. Nobahar M. Khavasi HR. Bazgir A. Tetrahedron 2012; 68: 1769
- 16 Wuts PG. M. Greene TW. Greene’s Protective Organic Synthesis . Wiley-Interscience; Hoboken: 2007. 4th ed. 814
- 17a Cintas P. Synlett 1995; 1087
- 17b Auge J. Lubin-Germain N. Uziel J. Synthesis 2007; 1739
- 18 Hutchins RO. In Encyclopedia of Reagents for Organic Synthesis . Paquette LA. Wiley; Chichester: 1995: 3202-3204
- 19 Huang W. Zhang X. Liu H. Shen J. Jiang H. Tetrahedron Lett. 2005; 46: 5965
- 20 Boyle WJ. Bunnett JF. J. Am. Chem. Soc. 1974; 96: 1418
- 21 Prices for powdered metals from the Aldrich catalogue: In (99.99%), 10 g/115.50 €; Mg (≥99%), 100 g/24.40 €; Zn (≥99%), 500 g/55.80 €.
- 22 Rama V. Kanagaraj K. Pitchumani K. J. Org. Chem. 2011; 76: 9090
- 23 Tisseh ZN. Dabiri M. Nobahar M. Khavasi HR. Bazgir A. Tetrahedron 2012; 68: 1769
- 24 Ahmed N. Siddiqui ZN. RSC Adv. 2015; 5: 16707
- 25 Katritzky AR. Cai C. Meher NK. Synthesis 2007; 1204
- 26 Suzuki H. Hwang YS. Nakaya C. Matano Y. Synthesis 1993; 1218
- 27 Kiselyov AS. Tetrahedron Lett. 2005; 46: 4851
- 28 Safaei-Ghomi J. Paymard-Samani S. Zahedi S. Shahbazi-Alavi H. Z. Naturforsch. B 2015; 70: 819
- 29 Maddila S. Naicker K. Momin MI. K. Rana S. Gorle S. Maddila S. Yalagala K. Singh M. Koorbanally NA. Jonnalagadda SB. Med. Chem. Res. 2016; 25: 283
See, for instance: