%0 Journal Article %1 ISI:000312231400027 %A Kazemi, Bagher %A Javanshir, Shahrzad %A Maleki, Ali %A Safari, Mostafa %A Khavasi, Hamid Reza %C THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND %D 2012 %I PERGAMON-ELSEVIER SCIENCE LTD %J TETRAHEDRON LETTERS %K Chromene; Dialkyl Malononitrile} Multicomponent Pyran; acetylenedicarboxylate; reaction; {Oxepine; %N 51 %P 6977-6981 %R 10.1016/j.tetlet.2012.10.046 %T An efficient synthesis of 4H-chromene, 4H-pyran, and oxepine derivatives via one-pot three-component tandem reactions %V 53 %X A new and efficient method has been developed for the synthesis of highly functionalized 2-amino-4H-pyran, 2-amino-4H-chromene, 2-amino-oxepine, and 2-hydroxy-oxepine derivatives through one-pot, three-component tandem reactions of structurally diverse 1,3-diketones, dialkyl acetylenedi-carboxylates, and malononitrile or ethyl cyanoacetate in the presence of a catalytic amount of Na2CO3 in ethanol. This efficient technique has the advantages of giving products in good to high yields, in short reaction times, and with a simple isolation procedure. (C) 2012 Elsevier Ltd. All rights reserved.

@article{ISI:000312231400027, abstract = {{A new and efficient method has been developed for the synthesis of highly functionalized 2-amino-4H-pyran, 2-amino-4H-chromene, 2-amino-oxepine, and 2-hydroxy-oxepine derivatives through one-pot, three-component tandem reactions of structurally diverse 1,3-diketones, dialkyl acetylenedi-carboxylates, and malononitrile or ethyl cyanoacetate in the presence of a catalytic amount of Na2CO3 in ethanol. This efficient technique has the advantages of giving products in good to high yields, in short reaction times, and with a simple isolation procedure. (C) 2012 Elsevier Ltd. All rights reserved.}}, added-at = {2017-05-10T15:29:29.000+0200}, address = {{THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}}, affiliation = {{Javanshir, S (Reprint Author), Iran Univ Sci \& Technol, Dept Chem, Tehran 1684613114, Iran. Kazemi, Bagher; Javanshir, Shahrzad; Maleki, Ali; Safari, Mostafa, Iran Univ Sci \& Technol, Dept Chem, Tehran 1684613114, Iran. Khavasi, Hamid Reza, Shahid Beheshti Univ, Dept Chem, Tehran 1983953113, Iran.}}, author = {Kazemi, Bagher and Javanshir, Shahrzad and Maleki, Ali and Safari, Mostafa and Khavasi, Hamid Reza}, author-email = {{shjavan@iust.ac.ir}}, biburl = {https://www.bibsonomy.org/bibtex/239737af341a459e57220c090be542dee/hkhavasi}, cited-references = {{Banerjee S, 2011, TETRAHEDRON, V67, P5717, DOI 10.1016/j.tet.2011.05.132. Boominathan M, 2011, TETRAHEDRON, V67, P6057, DOI 10.1016/j.tet.2011.06.021. Candenas ML, 2002, TETRAHEDRON, V58, P1921, DOI 10.1016/S0040-4020(02)00047-9. Ding DR, 2010, TETRAHEDRON LETT, V51, P1322, DOI 10.1016/j.tetlet.2009.12.139. Edrada RA, 1998, J NAT PROD, V61, P358, DOI 10.1021/np970276t. EVANS BE, 1988, J MED CHEM, V31, P2235, DOI 10.1021/jm00120a002. Fotouhi L, 2007, TETRAHEDRON LETT, V48, P5379, DOI 10.1016/j.tetlet.2007.06.035. Hewitt RJ, 2010, J ORG CHEM, V75, P955, DOI 10.1021/jo902306a. Javanshir S., 2011, J SAUDI CHEM SOC. Kaupp G, 2003, TETRAHEDRON, V59, P3753, DOI 10.1016/S0040-4020(03)00554-4. Li DZ, 2009, J ASIAN NAT PROD RES, V11, P613, DOI 10.1080/10286020902971029. Lu XH, 2011, EUR J ORG CHEM, P802, DOI 10.1002/ejoc.201000812. MACIAS FA, 1994, J ORG CHEM, V59, P8261, DOI 10.1021/jo00105a052. Maghsoodlou MT, 2003, MONATSH CHEM, V134, P1585, DOI 10.1007/s00706-003-0062-9. Mao S, 2008, J COMB CHEM, V10, P235, DOI 10.1021/cc7001843. MIKI I, 1992, JPN J PHARMACOL, V59, P357, DOI 10.1254/jjp.59.357. Moumou Y., 1992, PHYTOCHEMICAL, V62, P265. Naimi-Jamal MR, 2010, MOL DIVERS, V14, P473, DOI 10.1007/s11030-010-9246-5. Nicolaou KC, 2000, ANGEW CHEM INT EDIT, V39, P734, DOI 10.1002/(SICI)1521-3773(20000218)39:4<734::AID-ANIE734>3.3.CO;2-9. Poupaert J, 2005, CURR MED CHEM, V12, P877, DOI 10.2174/0929867053507388. Ramachary DB, 2010, J COMB CHEM, V12, P855, DOI 10.1021/cc100104k. Shaabani A, 2008, J ORG CHEM, V73, P3925, DOI 10.1021/jo8002612. Shaabani A, 2007, J ORG CHEM, V72, P6309, DOI 10.1021/jo0707131. Shaabani A, 2009, TETRAHEDRON, V65, P3492, DOI 10.1016/j.tet.2009.02.035. Snyder NL, 2006, TETRAHEDRON, V62, P9301, DOI 10.1016/j.tet.2006.07.021. Soria-Mercado IE, 2005, J NAT PROD, V68, P904, DOI 10.1021/np058011z. Sprogoe K, 2005, TETRAHEDRON, V61, P8718, DOI 10.1016/j.tet.2005.06.086. Stoe\&Cie, 2000, X STEP32 VERS 1 07B. Tandon VK, 2009, SYNLETT, P2992, DOI 10.1055/s-0029-1218006. Teimouri MB, 2006, TETRAHEDRON, V62, P3016, DOI 10.1016/j.tet.2006.01.039. Wurzel G., 1990, PLANTA MED, V31, P1239.}}, doc-delivery-number = {{052WR}}, doi = {{10.1016/j.tetlet.2012.10.046}}, funding-acknowledgement = {{Iran University of Science and Technology (IUST)}}, funding-text = {{We acknowledge the Iran University of Science and Technology (IUST) for partial financial support.}}, interhash = {7140e235b2c798ad9d16c50ed6f8cedb}, intrahash = {39737af341a459e57220c090be542dee}, issn = {{0040-4039}}, journal = {{TETRAHEDRON LETTERS}}, journal-iso = {{Tetrahedron Lett.}}, keywords = {Chromene; Dialkyl Malononitrile} Multicomponent Pyran; acetylenedicarboxylate; reaction; {Oxepine;}, keywords-plus = {{ISOCYANIDES; SCAFFOLD; ETHERS}}, language = {{English}}, month = {{DEC 19}}, number = {{51}}, number-of-cited-references = {{31}}, orcid-numbers = {{Maleki, Ali/0000-0001-5490-3350}}, pages = {{6977-6981}}, publisher = {{PERGAMON-ELSEVIER SCIENCE LTD}}, research-areas = {{Chemistry}}, times-cited = {{21}}, timestamp = {2017-05-10T15:29:29.000+0200}, title = {{An efficient synthesis of 4H-chromene, 4H-pyran, and oxepine derivatives via one-pot three-component tandem reactions}}, type = {{Article}}, unique-id = {{ISI:000312231400027}}, usage-count-last-180-days = {{1}}, usage-count-since-2013 = {{24}}, volume = {{53}}, web-of-science-categories = {{Chemistry, Organic}}, year = {{2012}} }