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Article: Application of bis(iminophosphorane) in heterocyclic synthesis: New entries to symmetrically or unsymmetrically substituted thieno[2,3-d:5,4-d′] dipyrimidine-4,5(3H,6H)-diones

TitleApplication of bis(iminophosphorane) in heterocyclic synthesis: New entries to symmetrically or unsymmetrically substituted thieno[2,3-d:5,4-d′] dipyrimidine-4,5(3H,6H)-diones
Authors
Issue Date2004
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/joc
Citation
Journal Of Organic Chemistry, 2004, v. 69 n. 24, p. 8366-8371 How to Cite?
AbstractThe bis(carbodiimides) 4, obtained from bis-aza-Wittig reactions of bis(iminophosphorane) 3 with 2 equiv of aromatic isocyanates, were reacted with secondary amine to give symmetrically substituted 2,7-diaminothieno[2,3-d:5,4- d′]dipyrimidine-4,5(3H,6H)-dione 6 in the presence of a catalytic amount of EtO-Na+. Reactions of 4 with phenols or ROH in the presence of a catalytic amount of potassium carbonate or RO-Na + gave symmetrically substituted 2,7-diaryl(alkyl)-oxythieno[2,3-d:5, 4-d′]dipyrimidine-4,5(3H,6H)-diones 6 in satisfactory yields. However, iminophosphoranes 9 were obtained via reaction of bis(iminophosphorane) 3 with 1 equiv of aromatic isocyanate and subsequent reaction with an amine in the presence of a catalytic amount of EtO-Na+. Further reaction of iminophosphoranes 9 with aromatic isocyanates and various nucleophile generated unsymmetrically substituted thieno[2,3-d:5,4-d′] dipyrimidine-4,5(3H,6H)-diones 12 in good yields.
Persistent Identifierhttp://hdl.handle.net/10722/182341
ISSN
2015 Impact Factor: 4.785
2015 SCImago Journal Rankings: 2.095
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorDing, MWen_US
dc.contributor.authorXu, SZen_US
dc.contributor.authorZhao, JFen_US
dc.date.accessioned2013-04-23T08:19:02Z-
dc.date.available2013-04-23T08:19:02Z-
dc.date.issued2004en_US
dc.identifier.citationJournal Of Organic Chemistry, 2004, v. 69 n. 24, p. 8366-8371en_US
dc.identifier.issn0022-3263en_US
dc.identifier.urihttp://hdl.handle.net/10722/182341-
dc.description.abstractThe bis(carbodiimides) 4, obtained from bis-aza-Wittig reactions of bis(iminophosphorane) 3 with 2 equiv of aromatic isocyanates, were reacted with secondary amine to give symmetrically substituted 2,7-diaminothieno[2,3-d:5,4- d′]dipyrimidine-4,5(3H,6H)-dione 6 in the presence of a catalytic amount of EtO-Na+. Reactions of 4 with phenols or ROH in the presence of a catalytic amount of potassium carbonate or RO-Na + gave symmetrically substituted 2,7-diaryl(alkyl)-oxythieno[2,3-d:5, 4-d′]dipyrimidine-4,5(3H,6H)-diones 6 in satisfactory yields. However, iminophosphoranes 9 were obtained via reaction of bis(iminophosphorane) 3 with 1 equiv of aromatic isocyanate and subsequent reaction with an amine in the presence of a catalytic amount of EtO-Na+. Further reaction of iminophosphoranes 9 with aromatic isocyanates and various nucleophile generated unsymmetrically substituted thieno[2,3-d:5,4-d′] dipyrimidine-4,5(3H,6H)-diones 12 in good yields.en_US
dc.languageengen_US
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/jocen_US
dc.relation.ispartofJournal of Organic Chemistryen_US
dc.subject.meshHeterocyclic Compounds - Chemical Synthesisen_US
dc.subject.meshKetones - Chemical Synthesisen_US
dc.subject.meshMolecular Structureen_US
dc.subject.meshOrganophosphorus Compounds - Chemical Synthesis - Chemistryen_US
dc.subject.meshPyrimidines - Chemical Synthesisen_US
dc.titleApplication of bis(iminophosphorane) in heterocyclic synthesis: New entries to symmetrically or unsymmetrically substituted thieno[2,3-d:5,4-d′] dipyrimidine-4,5(3H,6H)-dionesen_US
dc.typeArticleen_US
dc.identifier.emailZhao, JF: zhao0065@e.ntu.edu.sgen_US
dc.identifier.authorityZhao, JF=rp01745en_US
dc.description.naturelink_to_subscribed_fulltexten_US
dc.identifier.doi10.1021/jo048691ven_US
dc.identifier.pmid15549808-
dc.identifier.scopuseid_2-s2.0-9344263482en_US
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-9344263482&selection=ref&src=s&origin=recordpageen_US
dc.identifier.volume69en_US
dc.identifier.issue24en_US
dc.identifier.spage8366en_US
dc.identifier.epage8371en_US
dc.identifier.isiWOS:000225341300025-
dc.publisher.placeUnited Statesen_US
dc.identifier.scopusauthoridDing, MW=7202280967en_US
dc.identifier.scopusauthoridXu, SZ=7404439670en_US
dc.identifier.scopusauthoridZhao, JF=8393022100en_US

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