5-芳基四氮唑衍生物的高效合成方法与酯基的伴生降解
收稿日期: 2014-03-25
修回日期: 2014-04-25
网络出版日期: 2014-05-07
基金资助
国家自然科学基金(No. 21003018)资助项目.
An Efficient Approach to the Synthesis of 5-Aryl-1H-tetrazole Derivatives Accompanying with the Cleavage of Ester Group
Received date: 2014-03-25
Revised date: 2014-04-25
Online published: 2014-05-07
Supported by
Project supported by the National Natural Science Foundation of China (No. 21003018).
孙宏滨 , 孙源华 , 陈文龙 , 秦鹏 , 齐轩 . 5-芳基四氮唑衍生物的高效合成方法与酯基的伴生降解[J]. 有机化学, 2014 , 34(9) : 1889 -1894 . DOI: 10.6023/cjoc201403051
5-Phenyl-1H-tetrazoles were synthesized by catalytic [3+2] cycloaddition with aryl nitriles and sodium azide. Indium trichloride was used as an efficient catalyst. The tetrazoles binding with varieties of functional groups were synthesized in good to quantitative yields. This tetrazole synthetic protocol also showed remarkable de-carboxylation activity. Esters were cleaved to carboxylic acids or alcohols in one pot.
Key words： indium trichloride; catalysis; tetrazole; synthesis; [3+2] cycloaddition; cleavage of ester
[1] Herr, R.J.Bioorg.Med.Chem.2002, 10, 3379.
[2] Seki, M.Synthesis 2012, 3231.
[3] Fischer, N.; Karaghiosoff, K.; Klapotke, T.M.; Stierstorfer, J.Z.Anorg.Allg.Chem.2010, 636, 735.
[4] Seco, J.M.; Farias, M.D.; Bachs, N.M.; Caballero, A.B.; Salinas-Castillo, A.; Rodriguez-Dieguez, A.Inorg.Chim.Acta 2010, 363, 3194.
[5] Wang, X.L.; Li, N.; Tian, A.X.; Ying, J.; Zhao, D.; Liu, X.J.Inorg.Chem.Commun.2012, 25, 60.
[6] Odedra, A.; Seeberger, P.H.Angew.Chem., Int.Ed.2009, 48, 2699.
[7] Dai, L.; Cui, S.; Damu, G.L.V.; Zhou, C.Chin.J.Org.Chem.2013, 33, 224 (in Chinese).(代玲玲, 崔胜峰, Guli L.V.Damu, 周成合, 有机化学, 2013, 33, 224.)
[8] Finnegan, W.G.; Henry, R.A.; Lofquist, R.J.Am.Chem.Soc.1958, 80, 3908.
[9] Kumar, A.; Narayanan, R.; Shechter, H.J.Org.Chem.1996, 61, 4462.
[10] Jin, T.; Kitahara, F.; Kamijo, S.; Yamamoto, Y.Tetrahedron Lett.2008, 49, 2824.
[11] Jin, T.; Kitahara, F.; Kamijo, S.; Yamamoto, Y.Chem.-Asian J.2008, 3, 1575.
[12] Bonnamour, J.; Bolm, C.Chem.-Eur.J.2009, 15, 4543.
[13] Sreedhar, B.; Kumar, A.S.; Yada, D.Tetrahedron Lett.2011, 52, 3565.
[14] Curran, D.P.; Hadida, S.; Kim, S.-Y.Tetrahedron 1999, 55, 8997.
[15] Yao, Y.W.; Zhou, Y.; Lin, B.P.; Yao, C.Tetrahedron Lett.2013, 54, 6779.
[16] Gutmann, B.; Roduit, J.P.; Roberge, D.; Kappe, C.O.Angew.Chem., Int.Ed.2010, 49, 7101.
[17] Palde, P.B.; Jamison, T.F.Angew.Chem., Int.Ed.2011, 50, 3525.
[18] Demko, Z.P.; Sharpless, K.B.J.Org.Chem.2001, 66, 7945.
[19] Roh, J.; Vavrova, K.; Hrabalek, A.Eur.J.Org.Chem.2012, 6101.
[20] Lang, L.M.; Li, B.J.; Liu, W.; Jiang, L.; Xu, Z.; Yin, G.Chem.Commun.2010, 46, 448.
[21] Kantam, M.L.; Kumar, K.B.S.; Sridhar, C.Adv.Synth.Catal.2005, 347, 1212.
[22] Kantam, M.L.; Balasubrahmanyam, V.; Kumar, K.B.S.Synth.Commun.2006, 36, 1809.
[23] Kantam, M.L.; Kumar, K.B.S.; Raja, K.P.J.Mol.Catal.A: Chem.2006, 247, 186.
[24] Agawane, S.M.; Nagarkar, J.M.Catal.Sci.Technol.2012, 2, 1324.
[25] Habibi, D.; Nasrollahzadeh, M.Synth.Commun.2012, 42, 2023.
[26] He, J.H.; Li, B.J.; Chen, F.S.; Xu, Z.; Yin, G.J.Mol.Catal.A: Chem.2009, 304, 135.
[27] Nasrollahzadeh, M.; Bayat, Y.; Habibi, D.; Moshaee, S.Tetrahedron Lett.2009, 50, 4435.
[28] Qi, G.; Dai, Y.Chin.Chem.Lett.2010, 21, 1029.
[29] Qi, G.; Liu, W.; Bei, Z.N.Chin.J.Chem.2011, 29, 131.
[30] Chermahini, A.N.; Teimouri, A.; Momenbeik, F.; Zarei, A.; Dalirnasab, Z.; Ghaedi, A.; Roosta, M.J.Heterocycl.Chem.2010, 47, 913.
[31] Das, B.; Reddy, C.R.; Kumar, D.N.; Krishnaiah, M.; Narender, R.Synlett 2010, 391.
[32] Marvi, O.; Alizadeh, A.; Zarrabi, S.Bull.Korean Chem.Soc.2011, 32, 4001.
[33] Chauhan, K.K.; Frost, C.G.J.Chem.Soc., Perkin Trans.1 2000, 3015.
[34] Ranu, B.C.Eur.J.Org.Chem.2000, 2347.
[35] Fringuelli, F.; Piermatti, O.; Pizzo, F.; Vaccaro, L.Curr.Org.Chem.2003, 7, 1661.
[36] Sakai, N.; Konakahara, T.J.Synth.Org.Chem.Jpn.2011, 69, 38.
[37] Yadav, J.S.; Antony, A.; George, J.; Reddy, B.V.S.Eur.J.Org.Chem.2010, 591.
[38] Ghosh, R.; Maiti, S.J.Mol.Catal.A: Chem.2007, 264, 1.
[39] Goeta, A.; Salter, M.M.; Shah, H.Tetrahedron 2006, 62, 3582.
[40] Kumar, S.; Kaur, P.; Kumar, V.Curr.Org.Chem.2005, 9, 1205.
[41] Suresh, R.; Muthusubramanian, S.; Nagaraj, M.; Manickam, G.Tetrahedron Lett.2013, 54, 1779.
[42] Nagase, Y.; Shirai, H.; Kaneko, M.; Shirakawa, E.; Tsuchimoto, T.Org.Biomol.Chem.2013, 11, 1456.
[43] Mahato, S.K.; Vinayagam, J.; Dey, S.; Timiri, A.K.; Chatterjee, S.; Jaisankar, P.Aust.J.Chem.2013, 66, 241.
[44] Zhu, M.; Fu, W.J.; Xun, C.; Zou, G.L.Bull.Korean Chem.Soc.2012, 33, 43.
[45] Yanai, H.; Sakiyama, T.; Oguchi, T.; Taguchi, T.Tetrahedron Lett.2012, 53, 3161.
[46] Singh, M.S.; Raghuvanshi, K.Tetrahedron 2012, 68, 8683.
[47] Naidu, P.S.; Borah, P.; Bhuyan, P.J.Tetrahedron Lett.2012, 53, 4015.
[48] Khurana, J.M.; Chaudhary, A.; Nand, B.; Lumb, A.Tetrahedron Lett.2012, 53, 3018.
[49] Acharya, C.; Dey, S.; Jaisankar, P.Tetrahedron Lett.2012, 53, 5548.
[50] Yadav, J.S.; Reddy, B.V.S.; Reddy, P.M.K.; Dash, U.; Gupta, M.K.J.Mol.Catal.A: Chem.2007, 271, 266.
[51] Yadav, J.S.; Reddy, B.V.S.; Srinivas, R.; Maiti, A.J.Chem.Res., Synop.2001, 528.
[52] Sakai, N.; Usui, Y.; Ikeda, R.; Konakahara, T.Adv.Synth.Catal.2011, 353, 3397.
[53] Sun, H.B.; Chen, W.L.; Sun, Y.H.; Qin, P.; Qi, X.Adv.Mater.Res.2011, 396~398, 2416.
[54] Akhlaghinia, B.; Rezazadeh, S.J.Braz.Chem.Soc.2012, 23, 2197.
[55] Brookings, D.C.; Calmiano, M.D.; Gallimore, E.O.; Horsley, H.T.; Hutchings, M.C.; Johnson, J.A.; Kroeplien, B.; Lecomte, F.C.; Lowe, M.A.; Norman, T.J.; Porter, J.R.; Quincey, J.R.; Reuberson, J.T; Selby, M.D.; Shaw, M.A.; Zhu, Z.; Foley, A.M.WO 2013186229 [Chem.Abstr.2013, 160, 101301].
/
| 〈 |
|
〉 |
