- Synthesis of 11-methyl/phenyl-4,5-dihydro-3H-1,4-diazepinoindoles via Bischler-Napieralski type reaction
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A reaction of bromoacetone with N-cyanoethylanilines (1) gives 1-(2-cyanoethyl)-3-methylindoles (3a-d) directly while that of phenacyl bromide and 1 gives the intermediate N-cyanoethyl-N-phenacylanilines (2a-d).Cyclodehydration of 2 with P2O5 in xylene af
- Basanagoudar, L D,Mahajanshetti, C S,Dambal, S B
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p. 1018 - 1022
(2007/10/02)
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- 269. Intramolecular Carbenoid Reaction of Pyrrole Derivatives. Efficient Syntheses of Pyrrolizinone and Dihydroindolizinone
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The copper-catalyzed pyrolysis of 1-diazo-3-(pyrrol-1-yl)-2-propanone (1a) and 1-diazo-4-(pyrrol-1-yl)-2-butanone (1b) in benzene solution gave 1H-pyrrolizin-2-(3H)-one (4a) and 5,6-dihydroindolizin-7(8H)-one (4b), respectively, in quantative yield.Similar pyrolysis of 1-diazo-4-(3-methylindol-1-yl)-2-butanone (9) was less efficient giving 1-methylbenzo-5,6-dihydroindolizin-7(8H)-one (10) and 4-(3-methylindol-1-yl)-but-1-en-3-one (11) in 7percent and 24percent yield, respectively.
- Jefford, Charles W.,Johncock, William
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p. 2666 - 2671
(2007/10/02)
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- Palladium-Assisted N-Alkylation of Indoles: Attempted Application to Polycyclization
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The palladium(II) complexes of the olefins ethene, propene, and 1-hexene reacted with 1-lithioindole to produce N-alkylated indoles exclusively.Attempts to perform this N-alkylation intramoleculary (to form tricyclic material from 2-allylskatole) failed.Anilines with dienic side chains in the 2-position were subjected to Pd(II)-assisted cyclization conditions in attempts to induce polycyclization.However, only monocyclization was observed.
- Hegedus, Louis S.,Winton, Peter M.,Varaprath Sudarsanan
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p. 2215 - 2221
(2007/10/02)
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