2-Benzyloxymethyl-5-(tributylstannyl)tetrazole. A reagent for the preparation of 5-aryl- and 5-heteroaryl-1H-tetrazoles via the Stille reaction†

作者: Brett C Bookser

DOI: 10.1016/S0040-4039(00)00268-9

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摘要: Abstract 2-Benzyloxymethyl-5-(tributylstannyl)tetrazole (2) is a useful reagent for the conversion of aryl- and heteroaryl-halides (bromides iodides) to 5-aryl- 5-heteroaryl-1H-tetrazoles. The entails copper(I) iodide co-catalyzed Stille palladium-catalyzed cross-coupling reaction N-benzyloxymethyl deprotection step. Coupling was possible with electron neutral poor substrates in yields ranging from 35–93%.

参考文章(16)
Alex Andrus, James V. Heck, Burton G. Christensen, Beverly Partridge, Total synthesis of 3-(5-tetrazolyl)carbapenems Journal of the American Chemical Society. ,vol. 106, pp. 1808- 1811 ,(1984) , 10.1021/JA00318A042
David J. Carini, John V. Duncia, Paul E. Aldrich, Andrew T. Chiu, Alexander L. Johnson, Michael E. Pierce, William A. Price, Joseph B. Santella, Gregory J. Wells, Nonpeptide angiotensin II receptor antagonists: the discovery of a series of N-(biphenylylmethyl)imidazoles as potent, orally active antihypertensives. Journal of Medicinal Chemistry. ,vol. 34, pp. 2525- 2547 ,(1991) , 10.1021/JM00112A031
Alan R Katritzky, Charles W Rees, Eric FV Scriven, None, Comprehensive heterocyclic chemistry II Pergamon. ,(1996)
Masataka Yokoyama, Sachiko Hirano, Michio Matsushita, Takeshi Hachiya, Naoki Kobayashi, Misao Kubo, Hideo Togo, Hiroko Seki, Synthesis of tetrazoles bearing a sugar moiety (sugar tetrazoles). X-Ray molecular structure of ‘(7R,8R,9S,10R)-8,9,10-tribenzyloxy-7-benzyloxymethyl-6-oxa-1,5-pentamethylenetetrazole’ J. Chem. Soc., Perkin Trans. 1. pp. 1747- 1753 ,(1995) , 10.1039/P19950001747
Richard E. Holmes, Roland K. Robins, Purine Nucleosides. IX. The Synthesis of 9-β-D-Ribofuranosyl Uric Acid and Other Related 8-Substituted Purine Ribonucleosides1 Journal of the American Chemical Society. ,vol. 87, pp. 1772- 1776 ,(1965) , 10.1021/JA01086A028
John V. Duncia, Michael E. Pierce, Joseph B. Santella, Three synthetic routes to a sterically hindered tetrazole. A new one-step mild conversion of an amide into a tetrazole Journal of Organic Chemistry. ,vol. 56, pp. 2395- 2400 ,(1991) , 10.1021/JO00007A027
Kyu Yang Yi, Sung-eun Yoo, Synthesis of 5-aryl and vinyl tetrazoles by the palladium-catalyzed cross-coupling reaction Tetrahedron Letters. ,vol. 36, pp. 1679- 1682 ,(1995) , 10.1016/0040-4039(95)00129-Z
R.N. Butler, 4.13 – Tetrazoles Reference Module in Chemistry, Molecular Sciences and Chemical Engineering#R##N#Comprehensive Heterocyclic Chemistry. ,vol. 4, pp. 791- 838 ,(1984) , 10.1016/B978-008096519-2.00081-3