Transformation of indoline spiropyrans to bridged 1,3-benzoxazepino[3,2-a]indoles via 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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| Affiliation: | (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-benzoxazepino[3,2-a]indoles on treatment with a base. The mechanism of the rearrangement includes generation of a carbanion stabilized by a cyano group. __________ 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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