Reaction of huisgen zwitterion with 1,2-benzoquinones and isatins: Expeditious synthesis of dihydro-1,2,3-benzoxadiazoles and spirooxadiazolines

Organic Letters

Volumn 7, Issue 23, 2005, Pages 5139-5142

  Nair, Vijay ^a   Biju, A T ^a   Vinod, A U ^a   Suresh, Eringathodi ^b  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

^b CSIR CENTRAL SALT AND MARINE CHEMICALS RESEARCH INSTITUTE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOQUINONE DERIVATIVE; ISATIN; OXADIAZOLE DERIVATIVE; SPIRO COMPOUND;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; CONFORMATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

BENZOQUINONES; COMBINATORIAL CHEMISTRY TECHNIQUES; CRYSTALLOGRAPHY, X-RAY; ISATIN; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; OXADIAZOLES; SPIRO COMPOUNDS;

EID: 28244463319     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051956n     Document Type: Article

References (22)

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3. (c) Brunn, E.; Huisgen, R. Angew. Chem., Int. Ed. 1969, 8, 513.
4. Cookson, R. C.; Locke, J. M. J. Chem. Soc. 1963, 6062. The reaction of triphenylphosphine and DEAD with dimethyl acetylenedicarboxylate affording pyrazoles is mentioned; rationalization of this reaction as occurring via the zwitterion 3 was provided by Huisgen (ref 1.)
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17. +) 437.2605, found 437.2648.
18. 1H NMR spectra of the compound after exposure to air.
19. Crystal structure of compound 11a has been deposited at the Cambridge Crystallographic Data Center and allocated the reference no. CCDC 280314.
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21. See the Supporting Information for experimental details.
22. The crystal structure of compound 13a has been deposited at the Cambridge Crystallographic Data Center and allocated the reference no. CCDC 279798.