Transformation of indoline spiropyrans to bridged 1,3-benzoxazepino[3,2-<Emphasis Type="Italic">a</Emphasis>]indoles <Emphasis Type="Italic">via</Emphasis> carbanions stabilized by a cyano group |
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| Authors: | A Šačkus E Valaitytė V Amankavičienė U Berg C Schicktanz K Schlothauer |
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| Institution: | (1) Institute of Synthetic Chemistry, Kaunas University of Technology, Kaunas, LT-50254, Lithuania;(2) Organic Chemistry 1, Department of Chemistry, Lund University, 22100 Lund, Sweden;(3) Faculty of Informatics and Nature Sciences, University of Applied Sciences, 06217 Merseburg, Germany |
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| Abstract: | Condensation of 1-cyanomethyl-2,3,3-trimethyl-3H-indolium perchlorate with ortho-hydroxy-substituted aromatic aldehydes afforded
1-cyanomethylindoline spiropyrans. The latter underwent rearrangement to bridged 1,3-benzoxazepino3,2-a]indoles on treatment
with a base. The mechanism of the rearrangement includes generation of a carbanion stabilized by a cyano group.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1322–1328, September, 2007. |
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| Keywords: | carbanions 5a 13-methano-1 3-benzoxazepino[3 2-a]indoles spiropyrans cyclization |
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