A novel reaction between benzothiazoles and diaroylacetylenes in the presence of Meldrum's acid: ring expansion of benzothiazoles to functionalized 1,4-benzothiazines

Tetrahedron Letters

Volumn 50, Issue 31, 2009, Pages 4420-4422

  Adib, Mehdi ^a   Sheibani, Esmaeil ^a   Zhu, Long Guan ^b   Bijanzadeh, Hamid Reza ^c  

^a UNIVERSITY OF TEHRAN   (Iran)

^b ZHEJIANG UNIVERSITY   (China)

^c TARBIAT MODARES UNIVERSITY   (Iran)

Author keywords

Benzothiazoles; Diaroylacetylenes; Meldrum's acid; Ring expansion

Indexed keywords

1 (2,5 DIMETHYLPHENYL) 2 [2 (2,5 DIMETHYLPHENYL) 2 HYDROXY 2H 1,4 BENZOTHIAZIN 3 (4H)YLIDEN] 1 ETHANONE; 2 [2 HYDROXY 2 ARYL 2H 1,4 BENZOTHIAZIN 3(4H)YLIDEN] 1 ARYL 1 ETHANONE; 2 [2 HYDROXY 2 PHENYL 2H 1,4 BENZOTHIAZIN 3 (4H)YLIDEN] 1 PHENYL 1 ETHANONE; ACETYLENE DERIVATIVE; ACID; AMPHOLYTE; BENZOTHIAZOLE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CYCLOADDITION; DRUG DETERMINATION; DRUG SYNTHESIS; PRODUCTIVITY; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 67149084599     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.04.110     Document Type: Article

References (23)

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21. 3), 80.3 (C), 94.1 (CH), 118.3 (CH), 119.2 (C), 123.5, 127.3, 127.5, 128.1, 128.2, 129.9, 130.4 and 130.9 (8CH), 132.6 (C), 132.7 (CH), 133.3, 134.2, 135.0, 135.5, 136.1, 141.2 and 154.2 (7C), 196.5 (C{double bond, long}O).
22. 2 = 0.092. CCDC 719858 contains the supplementary crystallographic data for the structure reported in this Letter. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
23. The amount of formyl Meldrum's acid isolated from the reaction mixture of benzothiazole (2 mmol) and dibenzoylacetylene by column chromatography was 0.19 g, 55% (relative to benzothiazole).