%0 Journal Article %1 ISI:000279865700004 %A Teimouri, Mohammad Bagher %A Abbasi, Tayyebeh %A Khavasi, Hamid Reza %C PO BOX 314, ST ALBANS AL1 4ZG, HERTS, ENGLAND %D 2010 %I SCIENCE REVIEWS 2000 LTD %J JOURNAL OF CHEMICAL RESEARCH %K acetylenic alloxan; barbiturate; ester; gamma-butenolide; multicomponent reaction} {amine; %N 6 %P 310-314 %R 10.3184/030823410X12746990145128 %T Multicomponent tandem synthesis of oxospirobicyclic butenolidobarbiturates %X Novel oxospirobicyclic gamma-butenolides containing barbiturate moiety have been synthesised by the Michael-addition of primary amines to dialkyl acetylenedicarboxylates followed by aldol-like reaction with alloxan derivatives, and then gamma-lactonisation. Subsequent 1,4-addition of water and elimination of the amine group completes the sequence. This tandem reaction sequence represents a rapid and unprecedented route to the described biologically interesting molecules.

@article{ISI:000279865700004, abstract = {{Novel oxospirobicyclic gamma-butenolides containing barbiturate moiety have been synthesised by the Michael-addition of primary amines to dialkyl acetylenedicarboxylates followed by aldol-like reaction with alloxan derivatives, and then gamma-lactonisation. Subsequent 1,4-addition of water and elimination of the amine group completes the sequence. This tandem reaction sequence represents a rapid and unprecedented route to the described biologically interesting molecules.}}, added-at = {2017-05-10T15:29:29.000+0200}, address = {{PO BOX 314, ST ALBANS AL1 4ZG, HERTS, ENGLAND}}, affiliation = {{Teimouri, MB (Reprint Author), Iran Polymer \& Petrochem Inst, Petrochem Dept, POB 14965-115, Tehran, Iran. Teimouri, Mohammad Bagher, Iran Polymer \& Petrochem Inst, Petrochem Dept, Tehran, Iran. Abbasi, Tayyebeh, Univ Zanjan, Dept Chem, Zanjan, Iran. Khavasi, Hamid Reza, Shaheed Beheshti Univ, Dept Chem, Tehran, Iran.}}, author = {Teimouri, Mohammad Bagher and Abbasi, Tayyebeh and Khavasi, Hamid Reza}, author-email = {{m.teimouri@ippi.ac.ir}}, biburl = {https://www.bibsonomy.org/bibtex/2964099903c5b4b8b4fd854f21f3d7ae4/hkhavasi}, cited-references = {{ABIMAEL D, 1999, ORG LETT, V1, P337. BANDURRAGA MM, 1982, J AM CHEM SOC, V104, P6463, DOI 10.1021/ja00387a059. Beck B, 2001, ORG LETT, V3, P2875, DOI 10.1021/ol016328u. CAMER A, 1983, J HETEROCYCLIC CHEM, V20, P359. FEIT BA, 1986, J CHEM SOC PERK T 1, P2027, DOI 10.1039/p19860002027. Gunaskera G. P., 1996, J AM CHEM SOC, V118, P8759. HEGDE SG, 1993, J HETEROCYCLIC CHEM, V30, P1501. Hoye TR, 1999, ORG LETT, V1, P277, DOI 10.1021/ol9905912. HUISGEN R, 1966, CHEM BER-RECL, V99, P2526, DOI 10.1002/cber.19660990820. IRELAND RE, 1986, J ORG CHEM, V51, P635, DOI 10.1021/jo00355a013. Lee HJ, 1999, SYNTHETIC COMMUN, V29, P4375, DOI 10.1080/00397919908086600. Liras S, 2001, ORG LETT, V3, P703, DOI 10.1021/ol0070482. MURAI S, 1975, ANGEW CHEM INT EDIT, V14, P636, DOI 10.1002/anie.197506361. Nair V, 2000, SYNTHESIS-STUTTGART, P1713. Nozaki K, 1996, J ORG CHEM, V61, P4516, DOI 10.1021/jo951828k. RAO YS, 1976, CHEM REV, V76, P625, DOI 10.1021/cr60303a004. Rodriguez AD, 1998, J ORG CHEM, V63, P4425, DOI 10.1021/jo980256b. Rubin MB, 2000, CHEM REV, V100, P1121, DOI 10.1021/cr960079j. SAALFRANK RW, 1990, ANGEW CHEM INT EDIT, V29, P1041, DOI 10.1002/anie.199010411. Schank K, 2004, HELV CHIM ACTA, V87, P869, DOI 10.1002/hlca.200490085. Stanovnik B, 2004, CHEM REV, V104, P2433, DOI 10.1021/cr020093y. TEIMOURI MB, 2009, J CHEM RES, P522. Teimouri MB, 2008, TETRAHEDRON, V64, P10425, DOI 10.1016/j.tet.2008.08.039. Teimouri MB, 2010, TETRAHEDRON, V66, P259, DOI 10.1016/j.tet.2009.10.114. Teimouri MB, 2009, TETRAHEDRON, V65, P8120, DOI 10.1016/j.tet.2009.07.091. ZIMMER H, 1993, J HETEROCYCLIC CHEM, V30, P161. Ziyaei-Halimehjani A, 2008, TETRAHEDRON LETT, V49, P1244, DOI {[}10.1016/j.tetlet.2007.12.042, DOI 10.1016/J.TETLET.2007.12.042].}}, doc-delivery-number = {{625BF}}, doi = {{10.3184/030823410X12746990145128}}, funding-acknowledgement = {{Iran Polymer and Petrochemical Institute (IPPI) Research Council}}, funding-text = {{We would like to thank Iran Polymer and Petrochemical Institute (IPPI) Research Council for the financial support.}}, interhash = {b00e377818049f93c8a320e7ba5a09bd}, intrahash = {964099903c5b4b8b4fd854f21f3d7ae4}, issn = {{1747-5198}}, journal = {{JOURNAL OF CHEMICAL RESEARCH}}, journal-iso = {{J. Chem. Res}}, keywords = {acetylenic alloxan; barbiturate; ester; gamma-butenolide; multicomponent reaction} {amine;}, keywords-plus = {{DIMETHYL ACETYLENEDICARBOXYLATE; GAMMA-BUTYROLACTONES; FACILE SYNTHESIS; CHEMISTRY; DERIVATIVES; REACTIVITY; LACTONES}}, language = {{English}}, month = {{JUN}}, number = {{6}}, number-of-cited-references = {{27}}, pages = {{310-314}}, publisher = {{SCIENCE REVIEWS 2000 LTD}}, research-areas = {{Chemistry}}, times-cited = {{4}}, timestamp = {2017-05-10T15:29:29.000+0200}, title = {{Multicomponent tandem synthesis of oxospirobicyclic butenolidobarbiturates}}, type = {{Article}}, unique-id = {{ISI:000279865700004}}, usage-count-last-180-days = {{0}}, usage-count-since-2013 = {{2}}, web-of-science-categories = {{Chemistry, Multidisciplinary}}, year = {{2010}} }