Benzothiazines in synthesis. Eight-membered ring formation in an intramolecular Friedel-Crafts reaction

Tetrahedron Letters

Volumn 50, Issue 20, 2009, Pages 2326-2328

  Harmata, Michael ^a   Ying, Weijiang ^a   Barnes, Charles L ^a  

^a UNIVERSITY OF MISSOURI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOTHIADIAZINE DERIVATIVE; ELISAPTEROSIN B; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ARTICLE; FRIEDEL CRAFTS REACTION; HYDROLYSIS; NUCLEAR OVERHAUSER EFFECT; QUANTUM YIELD; STEREOCHEMISTRY; SYNTHESIS; X RAY ANALYSIS;

EID: 63349095635     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.02.227     Document Type: Article

References (23)

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18. 1H NMR data for crude reaction products.
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20. We did not explore the bromination of benzothiazine 15b as we could not obtain it in large amounts in pure form.
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22. Other experiments we have performed show that the reaction does not take place to any significant extent at -10 °C.
23. Crystallographic data (excluding structure factors) for some structures reported in this Letter have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 716164 (17a′) and 716143 (18). Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: +44(1223)336033; Email: deposit@ccdc.ac.uk].