Route towards new heteroaromatic benzo[1,4]dioxine derivatives

Chemistry Letters

Volumn 32, Issue 2, 2003, Pages 140-141

  Storsberg, Joachim ^a,c   Schollmeyer, Dieter ^a   Ritter, Helmut ^b  

^a JOHANNES GUTENBERG UNIVERSITY   (Germany)

^b HEINRICH HEINE UNIVERSITY   (Germany)

^c UNIVERSITY OF POTSDAM   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

3,4 DIHYDROXYTHIOPHENE; BENZENE DERIVATIVE; PYRROLE DERIVATIVE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; HALOGENATION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 0038221208     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2003.140     Document Type: Article

References (9)

1. H. Shirakawa, E. J. Louis, A. G. Mac Diarmid, C. K. Clang, and A. J. Heeger, J. Chem. Soc., Chem. Commun., 1977, 579.
2. L. Groenendaal, F. Jonas, D. Freitag, H. Pielartzik, and J. R. Reynolds, Adv. Mater., 12, 481 (2000).
3. 2, resulting in quantitative yield. 4 was prepared following the procedure of A. Merz, R. Schropp, and E. Dötterl, Synthesis, 1995, 795.
4. 2, resulting in quantitative yield. 4 was prepared following the procedure of A. Merz, R. Schropp, and E. Dötterl, Synthesis, 1995, 795.
5. The synthesis was performed in analogy to a procedure, described for substituted dibenzo[1,4]dioxines by a) G. C. Eastmond and J. Paprotny, Chem. Lett., 1999, 479. b) H. H. Lee and W. A. Denny, J. Chem. Soc., Perkin Trans. 1, 1990, 1071.
6. The synthesis was performed in analogy to a procedure, described for substituted dibenzo[1,4]dioxines by a) G. C. Eastmond and J. Paprotny, Chem. Lett., 1999, 479. b) H. H. Lee and W. A. Denny, J. Chem. Soc., Perkin Trans. 1, 1990, 1071.
7. max = 0.89. Figure 2: Thermal ellipsoid plot (50% probability level) of 2h. The molecule is flat. Selected bond lenghts (Å) and bond angles (°):S1-C2 1.706(2), S1-C5 1.712(2), C3-O6 1.377(2), O6-C7 1.381(2), C4-O9 1.376(2), O9-C8 1.376(2), C11-C14 1.438(2), C14-N15 1.140(3), C2-S1-C5 92.73(9), C3-O6-C7 114.3(1), C4-O9-C8 114.7(1), C11-C14-N15 179.8(2).
8. #-14(2).
9. +). Some compounds were also characterized by single crystal X-ray crystallography. The Crystallographic data have been deposited with the Cambridge Crystallographic Data Centre as a supplementary publication. Copies of this data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB21EZ, UK; fax: (+44)1223 336033; e-mail: deposit@ccdc.cam.ac.uk.