Journal
JOURNAL OF HETEROCYCLIC CHEMISTRY
Volume 43, Issue 1, Pages 177-181Publisher
HETERO CORPORATION
DOI: 10.1002/jhet.5570430127
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Synthesis of new azonia derivatives of thia[6]helicene (1) and thia[7]helicene (2) is described. The Knoevenagel condensation of 2-methylbenzothieno[3,2-a]quinolizinium salt (8) with appropriate arylaldehydes yielded 2-(arylvinyl)benzothieno[3,2-a]quinolizinium salts (9 and 10). respectively. Photocyclization of 2-styrylbenzothieno[3,2-a]quinolizinium salt (8) gave 7a-azonia-5-thia[6]helicene (1) in 63% yield. Similarly, 2-[2-(2-naphthyl)vinyl]benzothieno[3,2-a]quinolizinium salt (10) afforded 7a-azonia-5thia[7]helicene (2) in 56% yield. The complete and unambiguous assignment of their H-1- and C-13-nmr spectra was performed by utilizing two-dimensional nmr spectroscopic methods.
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