Gold catalyzed intramolecular cyclization of (2-aminophenyl)-cyclopropyl methanols as an expedient route to 2,3-dihydro-1h-benzazepines and indolines.
We reported herein an efficient synthetic route of 2,3-dihydro-1H-benzazepines and indolines that relies on (4-CF3Ph)3PAuCl/AgOTf catalyzed intramolecular hydroamination of cyclopropyl methanols containing an aniline moiety. The methodology is applicable to a wide range of electron-donating, elec...
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sg-ntu-dr.10356-399332023-02-28T23:15:26Z Gold catalyzed intramolecular cyclization of (2-aminophenyl)-cyclopropyl methanols as an expedient route to 2,3-dihydro-1h-benzazepines and indolines. Susanti, Dewi. Philip Wai Hong Chan School of Physical and Mathematical Sciences DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis We reported herein an efficient synthetic route of 2,3-dihydro-1H-benzazepines and indolines that relies on (4-CF3Ph)3PAuCl/AgOTf catalyzed intramolecular hydroamination of cyclopropyl methanols containing an aniline moiety. The methodology is applicable to a wide range of electron-donating, electron-withdrawing, and sterically demanding substituted (2-aminophenyl)-cyclopropyl methanol substrates that gave the corresponding 2,3-dihydro-1H-benzazepine and indoline products in yields of 23-92%. The mechanism is suggested to involve activation of hydroxyl group of the substrate by (4-CF3Ph)3PAuCl/AgOTf followed by ring opening of the cyclopropane moiety. Intramolecular cyclization in a 7-endo-trig manner of intermediates derived from unactivated cyclopropyl methanols furnished the 2,3-dihydro-1H-benzazepine. On the other hand, intramolecular hydroamination of intermediates derived from activated cyclopropyl methanols underwent 5-endo-trig cyclization to give the indoline products. Bachelor of Science in Chemistry and Biological Chemistry 2010-06-08T03:25:50Z 2010-06-08T03:25:50Z 2010 2010 Final Year Project (FYP) http://hdl.handle.net/10356/39933 en 44 p. application/pdf |
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DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis Susanti, Dewi. Gold catalyzed intramolecular cyclization of (2-aminophenyl)-cyclopropyl methanols as an expedient route to 2,3-dihydro-1h-benzazepines and indolines. |
description |
We reported herein an efficient synthetic route of 2,3-dihydro-1H-benzazepines and
indolines that relies on (4-CF3Ph)3PAuCl/AgOTf catalyzed intramolecular hydroamination of
cyclopropyl methanols containing an aniline moiety. The methodology is applicable to a wide
range of electron-donating, electron-withdrawing, and sterically demanding substituted
(2-aminophenyl)-cyclopropyl methanol substrates that gave the corresponding
2,3-dihydro-1H-benzazepine and indoline products in yields of 23-92%. The mechanism is
suggested to involve activation of hydroxyl group of the substrate by (4-CF3Ph)3PAuCl/AgOTf
followed by ring opening of the cyclopropane moiety. Intramolecular cyclization in a 7-endo-trig
manner of intermediates derived from unactivated cyclopropyl methanols furnished the
2,3-dihydro-1H-benzazepine. On the other hand, intramolecular hydroamination of
intermediates derived from activated cyclopropyl methanols underwent 5-endo-trig cyclization
to give the indoline products. |
author2 |
Philip Wai Hong Chan |
author_facet |
Philip Wai Hong Chan Susanti, Dewi. |
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Final Year Project |
author |
Susanti, Dewi. |
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Susanti, Dewi. |
title |
Gold catalyzed intramolecular cyclization of (2-aminophenyl)-cyclopropyl methanols as an expedient route to 2,3-dihydro-1h-benzazepines and indolines. |
title_short |
Gold catalyzed intramolecular cyclization of (2-aminophenyl)-cyclopropyl methanols as an expedient route to 2,3-dihydro-1h-benzazepines and indolines. |
title_full |
Gold catalyzed intramolecular cyclization of (2-aminophenyl)-cyclopropyl methanols as an expedient route to 2,3-dihydro-1h-benzazepines and indolines. |
title_fullStr |
Gold catalyzed intramolecular cyclization of (2-aminophenyl)-cyclopropyl methanols as an expedient route to 2,3-dihydro-1h-benzazepines and indolines. |
title_full_unstemmed |
Gold catalyzed intramolecular cyclization of (2-aminophenyl)-cyclopropyl methanols as an expedient route to 2,3-dihydro-1h-benzazepines and indolines. |
title_sort |
gold catalyzed intramolecular cyclization of (2-aminophenyl)-cyclopropyl methanols as an expedient route to 2,3-dihydro-1h-benzazepines and indolines. |
publishDate |
2010 |
url |
http://hdl.handle.net/10356/39933 |
_version_ |
1759855893595291648 |