%0 Journal Article %1 ISI:000343116100012 %A Abaee, M. Saeed %A Akbarzadeh, Elahe %A Shockravi, Abbas %A Mojtahedi, Mohammad M. %A Khavasi, Hamid Reza %C 65 AURIGA DR, SUITE 203, OTTAWA, ON K2E 7W6, CANADA %D 2014 %I CANADIAN SCIENCE PUBLISHING, NRC RESEARCH PRESS %J CANADIAN JOURNAL OF CHEMISTRY %K ZrO2 catalyst; diastereoselectivity} multicomponent nano reaction; {Mannich %N 7 %P 659-664 %R 10.1139/cjc-2013-0410 %T Nano ZrO2: an efficient, recyclable, and inexpensive catalyst for diastereoselective three-component Mannich reactions %V 92 %X A facile procedure is developed for the three-component Mannich reactions of several heterocyclic, homocyclic, and acyclic ketones by using catalytic quantities of nano ZrO2. As a result, the starting ketones undergo rapid reactions with a variety of aromatic aldehydes and aniline derivatives at room temperature to produce stereoselectively high yields of the corresponding anti beta-amino ketones. Interestingly, the catalyst could be recycled for several runs in a row without significant loss of its activity. The structure of the products was assigned based on their spectroscopic data and the anti stereoselectivity was confirmed by X-ray crystallography.

@article{ISI:000343116100012, abstract = {{A facile procedure is developed for the three-component Mannich reactions of several heterocyclic, homocyclic, and acyclic ketones by using catalytic quantities of nano ZrO2. As a result, the starting ketones undergo rapid reactions with a variety of aromatic aldehydes and aniline derivatives at room temperature to produce stereoselectively high yields of the corresponding anti beta-amino ketones. Interestingly, the catalyst could be recycled for several runs in a row without significant loss of its activity. The structure of the products was assigned based on their spectroscopic data and the anti stereoselectivity was confirmed by X-ray crystallography.}}, added-at = {2017-05-10T15:29:29.000+0200}, address = {{65 AURIGA DR, SUITE 203, OTTAWA, ON K2E 7W6, CANADA}}, affiliation = {{Abaee, MS (Reprint Author), Chem \& Chem Engn Res Ctr Iran, POB 14335-186, Tehran, Iran. Abaee, M. Saeed; Mojtahedi, Mohammad M., Chem \& Chem Engn Res Ctr Iran, Tehran, Iran. Akbarzadeh, Elahe; Shockravi, Abbas, Kharazmi Univ, Dept Chem, Tehran 1571914911, Iran. Khavasi, Hamid Reza, Shahid Beheshti Univ, Fac Chem, Tehran 1983963113, Iran.}}, author = {Abaee, M. Saeed and Akbarzadeh, Elahe and Shockravi, Abbas and Mojtahedi, Mohammad M. and Khavasi, Hamid Reza}, author-email = {{abaee@ccerci.ac.ir abbas\_shockravi@yahoo.co.uk}}, biburl = {https://www.bibsonomy.org/bibtex/2f18e0ec7a6453ce90b49265475ad1d87/hkhavasi}, cited-references = {{Abaee MS, 2012, J HETEROCYCLIC CHEM, V49, P1346, DOI 10.1002/jhet.976. Abaee MS, 2012, SYNLETT, P2073, DOI 10.1055/s-0031-1290438. Abaee MS, 2012, TETRAHEDRON LETT, V53, P4405, DOI 10.1016/j.tetlet.2012.06.040. Akiyama T, 2005, SYNLETT, P322, DOI 10.1055/s-2004-836062. Choudhury LH, 2011, TETRAHEDRON, V67, P8213, DOI 10.1016/j.tet.2011.07.020. Clarke PA, 2006, EUR J ORG CHEM, P2045, DOI 10.1002/ejoc.200500964. Cordova A, 2004, ACCOUNTS CHEM RES, V37, P102, DOI 10.1021/ar030231l. Domling A, 2012, CHEM REV, V112, P3083, DOI 10.1021/cr100233r. Guo QX, 2007, J AM CHEM SOC, V129, P3790, DOI 10.1021/ja068236b. Guo QS, 2013, ORG LETT, V15, P508, DOI 10.1021/ol303315c. Harms Klaus, 2012, Acta Crystallogr Sect E Struct Rep Online, V68, po749, DOI 10.1107/S1600536812005983. Hayashi Y, 2005, TETRAHEDRON, V61, P11393, DOI 10.1016/j.tet.2005.09.013. Hirose T, 2006, TETRAHEDRON LETT, V47, P6761, DOI 10.1016/j.tetlet.2006.07.083. Jacobine AM, 2012, TETRAHEDRON, V68, P7799, DOI 10.1016/j.tet.2012.07.039. Kang D, 2012, ORG LETT, V14, P3912, DOI 10.1021/ol301660f. Kano T, 2012, J AM CHEM SOC, V134, P7516, DOI 10.1021/ja301120z. Li H, 2009, TETRAHEDRON LETT, V50, P6858, DOI 10.1016/j.tetlet.2009.09.131. Lin YF, 2012, J COLLOID INTERF SCI, V368, P660, DOI 10.1016/j.jcis.2011.11.055. Mannich C., 1917, ARCH PHARM, V255, P261, DOI DOI 10.1002/ARDP.19172550217. Mojtahedi MM, 2006, CAN J CHEM, V84, P429, DOI 10.1139/V06-024. Mukhopadhyay C, 2009, TETRAHEDRON LETT, V50, P4246, DOI 10.1016/j.tetlet.2009.04.135. Ollevier T, 2006, TETRAHEDRON LETT, V47, P8351, DOI 10.1016/j.tetlet.2006.09.082. Pellissier H, 2009, TETRAHEDRON, V65, P2839, DOI 10.1016/j.tet.2009.01.068. Rai US, 2010, EUR J MED CHEM, V45, P6090, DOI 10.1016/j.ejmech.2010.09.015. Rasalkar MS, 2007, CAN J CHEM, V85, P77, DOI 10.1139/V06-176. Sharghi H, 2010, CAN J CHEM, V88, P14, DOI 10.1139/V09-141. Xavier NM, 2008, CARBOHYD RES, V343, P1523, DOI 10.1016/j.carres.2008.04.033. Yang CF, 2012, ORG LETT, V14, P3092, DOI 10.1021/ol301180z. Yang J, 2013, J ORG CHEM, V78, P1230, DOI 10.1021/jo302404v. Zhu J, 2005, MULTICOMPONENT REACTIONS, P1, DOI 10.1002/3527605118.}}, doc-delivery-number = {{AQ8VV}}, doi = {{10.1139/cjc-2013-0410}}, eissn = {{1480-3291}}, funding-acknowledgement = {{Ministry of Science, Research, and Technology of Iran}}, funding-text = {{The Ministry of Science, Research, and Technology of Iran is gratefully acknowledged for partial financial support of this work.}}, interhash = {826e722bafc914663409b5add3e45d75}, intrahash = {f18e0ec7a6453ce90b49265475ad1d87}, issn = {{0008-4042}}, journal = {{CANADIAN JOURNAL OF CHEMISTRY}}, journal-iso = {{Can. J. Chem.}}, keywords = {ZrO2 catalyst; diastereoselectivity} multicomponent nano reaction; {Mannich}, keywords-plus = {{AMINO CARBONYL-COMPOUNDS; ONE-POT; STEREOSELECTIVE-SYNTHESIS; TANDEM ALDOL; ACID; SYSTEM; CHEMISTRY}}, language = {{English}}, month = {{JUL}}, number = {{7}}, number-of-cited-references = {{30}}, pages = {{659-664}}, publisher = {{CANADIAN SCIENCE PUBLISHING, NRC RESEARCH PRESS}}, research-areas = {{Chemistry}}, times-cited = {{3}}, timestamp = {2017-05-10T15:29:29.000+0200}, title = {{Nano ZrO2: an efficient, recyclable, and inexpensive catalyst for diastereoselective three-component Mannich reactions}}, type = {{Article}}, unique-id = {{ISI:000343116100012}}, usage-count-last-180-days = {{0}}, usage-count-since-2013 = {{5}}, volume = {{92}}, web-of-science-categories = {{Chemistry, Multidisciplinary}}, year = {{2014}} }