- Synthesis of highly N-substituted indole library via conjugate additions of indoline and their synthetic tool potentials
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A comprehensive library of N- or 1-substituted indoles was formed by conjugate additions of indoline with Michael acceptors followed by an oxidation step. Using N-substituted indoles as key Michael donors, the synthesis of 1,3-disubstituted indoles was al
- Kilic, Haydar,Bayindir, Sinan,Erdogan, Esra,Saracoglu, Nurullah
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experimental part
p. 5619 - 5630
(2012/09/08)
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- Addition of secondary amines to maleamic esters and maleimides
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Contrary to some literature claims, secondary amines such as piperidine or their acetates do not promote the cyclization of maleanilic esters with activated orthoalkyl groups to form 2-quinolones, but instead they add to the maleic double bond, to produce 3-aminosuccinimides or 3-aminosuccinamic esters, depending on the conditions used. This and similar reactions were studied and also an alternative synthesis of 7-nitro-3-(2-oxo-2-piperidin-1-ylethyl)-3,4-dihydroquinolin-2(1H)-one was achieved utilizing the Schmidt reaction as the key step. Copyright Acta Chemica Scandinavica 1999.
- Bergman, Jan,Brimert, Thomas
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- Photoreactions of 2-(N-alkylarylamino) succinimides and related compounds
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On irradiation (254 nm), 2-(N-methylanilino)-N-phenylsuccinimide (6a) underwent homolysis of the C(2)-N bond to yield fission products N-methylaniline and N-phenylsuccinimide (12), along with the products of ortho- and para-rearrangement 2-[2-(N-methylamino)phenyl]-N-phenylsuccinimide (13) and 2-[4- (N-methylamino)phenyl]-N-phenylsuccinimide (14a) respectively. Similarly, irradiation of 2-(N-methyl- anilino)succinimide (6b) and N-benzyl-2-(N-methylanilino)succinimide (6c) gave N-methylaniline and the corresponding products of para-rearrangement. In contrast, both fission and type II cyclisation photo-products 12 and 17 respectively were formed from N-phenyl-2-(1,2,3,4-tetrahydroquinolin-1-yl)succinimide (16) and only the type II cyclisation product 1-hydroxy-2,7-diphenyl-2,7-diazabicyclo-[3.3.0]octan-3-one (21) was obtained from 2-(N-methylanilinomethyl)-N-phenylsuccinimide (20).
- Ashraf, Syed A.,Hill, John,M'Hamedi, Ahmed,Zerizer, Hafiza
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p. 6747 - 6756
(2007/10/02)
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