%0 Journal Article %1 ISI:000370906600009 %A Alizadeh, Abdolali %A Vahabi, Amir Hossein %A Bazgir, Ayoob %A Khavasi, Hamid Reza %A Zhu, Zhe %A Zhu, Long-Guan %C THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND %D 2016 %I PERGAMON-ELSEVIER SCIENCE LTD %J TETRAHEDRON %K Cyclic Functionalized Ketene Tetra bicyclic dithioacetal; guanidines} salt; substituted thiophenes; thioureas; {Organic %N 10 %P 1342-1350 %R 10.1016/j.tet.2016.01.031 %T Determinative role of ring size and substituents in highly selective synthesis of functionalized bicyclic guanidine and tetra substituted thiophene derivatives based on salt adducts afforded by cyclic thioureas and ketene dithioacetal %V 72 %X The condensation of organic salt adducts generated by cyclic thioureas and 2-di(methylsulfanyl)methylenemalononitrile with dialkyl acetylenedicarboxylates selectively leads to either tetrasubstituted thiophenes (2 examples) or hitherto unreported bicyclic guanidine (13 examples) derivatives, with controlling factors being ring size, the substituent on the S- methylisothioureaand the bulk of the substituent on the dialkyl acetylenedicarboxylates. Green solvents, short reaction time; easy purification, high yield and selectivity, are key feature of this protocol in the condensation step. The performances of the reactions in the presence of free-base and a catalyst at room temperature is unprecedented in the synthesis of thiophene frameworks and functionalized bicyclic guanidine scaffolds. (C) 2016 Elsevier Ltd. All rights reserved.

@article{ISI:000370906600009, abstract = {{The condensation of organic salt adducts generated by cyclic thioureas and 2-di(methylsulfanyl)methylenemalononitrile with dialkyl acetylenedicarboxylates selectively leads to either tetrasubstituted thiophenes (2 examples) or hitherto unreported bicyclic guanidine (13 examples) derivatives, with controlling factors being ring size, the substituent on the S- methylisothioureaand the bulk of the substituent on the dialkyl acetylenedicarboxylates. Green solvents, short reaction time; easy purification, high yield and selectivity, are key feature of this protocol in the condensation step. The performances of the reactions in the presence of free-base and a catalyst at room temperature is unprecedented in the synthesis of thiophene frameworks and functionalized bicyclic guanidine scaffolds. (C) 2016 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 = {{Alizadeh, A (Reprint Author), Tarbiat Modares Univ, Dept Chem, POB 14115-175, Tehran, Iran. Alizadeh, Abdolali; Vahabi, Amir Hossein, Tarbiat Modares Univ, Dept Chem, POB 14115-175, Tehran, Iran. Bazgir, Ayoob; Khavasi, Hamid Reza, Shahid Beheshti Univ, Dept Chem, Tehran 1983963113, Iran. Zhu, Zhe, Zhejiang Univ, Dept Polymer Sci \& Engn, Hangzhou 310027, Zhejiang, Peoples R China. Zhu, Long-Guan, Zhejiang Univ, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China.}}, author = {Alizadeh, Abdolali and Vahabi, Amir Hossein and Bazgir, Ayoob and Khavasi, Hamid Reza and Zhu, Zhe and Zhu, Long-Guan}, author-email = {{aalizadeh@modares.ac.ir}}, biburl = {https://www.bibsonomy.org/bibtex/20871373beae24f5763d7b56e86a8fd1a/hkhavasi}, cited-references = {{Berlinck RGS, 2008, NAT PROD REP, V25, P919, DOI 10.1039/b507874c. 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Yu HH, 2004, ANGEW CHEM INT EDIT, V43, P3700, DOI 10.1002/anie.200453896.}}, doc-delivery-number = {{DE8SI}}, doi = {{10.1016/j.tet.2016.01.031}}, funding-acknowledgement = {{Tarbiat Modares University; Shahid Beheshti University, Iran}}, funding-text = {{Financial support of this research from Tarbiat Modares University and Shahid Beheshti University, Iran is gratefully acknowledged.}}, interhash = {876949ab7a79aef265bc164522d9c84d}, intrahash = {0871373beae24f5763d7b56e86a8fd1a}, issn = {{0040-4020}}, journal = {{TETRAHEDRON}}, journal-iso = {{Tetrahedron}}, keywords = {Cyclic Functionalized Ketene Tetra bicyclic dithioacetal; guanidines} salt; substituted thiophenes; thioureas; {Organic}, keywords-plus = {{HENRY REACTION; INHIBITORS; DESIGN; CONDENSATION; EFFICIENT; SYSTEMS; TBD}}, language = {{English}}, month = {{MAR 10}}, number = {{10}}, number-of-cited-references = {{37}}, pages = {{1342-1350}}, publisher = {{PERGAMON-ELSEVIER SCIENCE LTD}}, research-areas = {{Chemistry}}, times-cited = {{0}}, timestamp = {2017-05-10T15:29:29.000+0200}, title = {{Determinative role of ring size and substituents in highly selective synthesis of functionalized bicyclic guanidine and tetra substituted thiophene derivatives based on salt adducts afforded by cyclic thioureas and ketene dithioacetal}}, type = {{Article}}, unique-id = {{ISI:000370906600009}}, usage-count-last-180-days = {{5}}, usage-count-since-2013 = {{19}}, volume = {{72}}, web-of-science-categories = {{Chemistry, Organic}}, year = {{2016}} }