caa a22 4500 467920052 CHVBK 20180406152914.0 cr unu---uuuuu 170328e20060801xx s 000 0 eng 10.1007/s00706-005-0504-7 doi (NATIONALLICENCE)springer-10.1007/s00706-005-0504-7 Cyclization of Nitrospirobenzopyrans to Bridged Benzoxazepino[3,2- a ]indoles [Elektronische Daten] [Neringa Kleizienė, Virginė Amankavičienė, Ulf Berg, Carsten Schicktanz, Klaus Schlothauer, Algirdas Šačkus] Summary.: Condensation of 1-substituted 1,2,3,9a-tetrahydro-9H-imidazo[1,2-a]indol-2-ones with 5-nitrosalicylaldehyde afforded 1′-[(N-monosubstituted carbamoyl)methyl]indoline nitrospirobenzopyrans. Treatment of the latter with strong base led to the formation of a mixture of cis/trans-5a,13-methano-1,3-benzoxazepino[3,2-a]indoles. Results of semiempirical calculations gave evidence that such a transformation of nitrospirobenzopyrans to bicyclic indole derivatives could proceed via a single transition state, where the negatively charged carbon atom attacks the vinylic double bond of the spiropyran system. Springer-Verlag, 2006 Keywords. Heterocycles nationallicence Indoles nationallicence Nitrospiropyrans nationallicence Carbanions nationallicence 5a,13-Methano-1,3-benzoxazepino[3,2- a ]indoles nationallicence Kleizienė Neringa Department of Organic Chemistry, Kaunas University of Technology, Kaunas, Lithuania aut Amankavičienė Virginė Department of Organic Chemistry, Kaunas University of Technology, Kaunas, Lithuania aut Berg Ulf Organic Chemistry 1, Department of Chemistry, Lund University, Lund, Sweden aut Schicktanz Carsten Faculty of Informatics and Nature Sciences, University of Applied Nature Sciences, Merseburg, Germany aut Schlothauer Klaus Faculty of Informatics and Nature Sciences, University of Applied Nature Sciences, Merseburg, Germany aut Šačkus Algirdas Department of Organic Chemistry, Kaunas University of Technology, Kaunas, Lithuania aut Monatshefte für Chemie / Chemical Monthly Springer-Verlag 137/8(2006-08-01), 1109-1117 0026-9247 137:8<1109 2006 137 706 https://doi.org/10.1007/s00706-005-0504-7 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s00706-005-0504-7 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Kleizienė Neringa Department of Organic Chemistry, Kaunas University of Technology, Kaunas, Lithuania aut NATIONALLICENCE 700 1- Amankavičienė Virginė Department of Organic Chemistry, Kaunas University of Technology, Kaunas, Lithuania aut NATIONALLICENCE 700 1- Berg Ulf Organic Chemistry 1, Department of Chemistry, Lund University, Lund, Sweden aut NATIONALLICENCE 700 1- Schicktanz Carsten Faculty of Informatics and Nature Sciences, University of Applied Nature Sciences, Merseburg, Germany aut NATIONALLICENCE 700 1- Schlothauer Klaus Faculty of Informatics and Nature Sciences, University of Applied Nature Sciences, Merseburg, Germany aut NATIONALLICENCE 700 1- Šačkus Algirdas Department of Organic Chemistry, Kaunas University of Technology, Kaunas, Lithuania aut NATIONALLICENCE 773 0- Monatshefte für Chemie / Chemical Monthly Springer-Verlag 137/8(2006-08-01), 1109-1117 0026-9247 137:8<1109 2006 137 706 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer