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Article Abstract
[reaction: see text] A novel one-pot synthesis of indole systems via tandem hydroformylation/Fischer indole synthesis starting from olefins and arylhydrazines is described. This tandem procedure leads directly to 3-substituted indoles if unsubstituted phenylhydrazine is used and to 3,5- respectively 3,7-disubstituted indoles if para- or ortho-substituted arylhydrazines are used.
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Application of iridium catalyzed allylic substitution reactions in the synthesis of branched tryptamines and homologues via tandem hydroformylation-Fischer indole synthesis.
Org Biomol Chem
October 2008
Technische Universität Dortmund, Fachbereich Chemie, Organische Chemie I, Otto-Hahn-Str. 6, 44227 Dortmund.
Combination of enantioselective allylation reactions with a tandem hydroformylation-Fischer indole synthesis sequence as a highly diversity-oriented strategy for the synthesis of tryptamines and homologues was explored. This modular approach allows the substituents at C3 of the indole core, the type of the amine moiety, and the distance of the amine moiety to the indole core in the final synthetic step to be defined. The starting materials required for the hydroformylation step were synthesized via iridium catalyzed enantioselective allylic substitution reactions in high yields and excellent enantioselectivities.
View Article and Find Full Text PDF2,3-Disubstituted indoles from olefins and hydrazines via tandem hydroformylation-Fischer indole synthesis and skeletal rearrangement.
Org Biomol Chem
January 2006
Fachbereich Chemie, Organische Chemie I, Universität Dortmund, Otto-Hahn-Str. 6, 44227 Dortmund, Germany.
The tandem hydroformylation-Fischer indolisation protocol is used in the synthesis of 2,3-disubstituted indoles. After hydroformylation of selected olefins to form alpha-branched aldehydes in a one-pot procedure these are condensed with phenylhydrazine to give hydrazones. Upon acid-promoted [3,3]-sigmatropic rearrangement indolenine intermediates with quaternary centres in the 3-position are formed, which, after selective Wagner-Meerwein-type rearrangement of one of the substituents from the 3- to the 2-position, lead to 2,3-disubstituted indoles.
View Article and Find Full Text PDFSynthesis of pharmacologically relevant indoles with amine side chains via tandem hydroformylation/Fischer indole synthesis.
J Org Chem
July 2005
Fachbereich Chemie, Organische Chemie I, Universität Dortmund, Otto-Hahn-Strasse 6, 44227 Dortmund.
[reaction: see text] The sequence of hydroformylation and Fischer indole synthesis starting from amino olefins and aryl hydrazines is described. In a convergent manner, the two units bearing pharmacologically relevant substituents are assembled in the final indolization step. This modular and diversity-oriented approach to tryptamines and homotryptamines can be conducted in water and allows synthesis of branched and nonbranched tryptamines as well as tryptamine-based pharmaceuticals such as the 5-HT1D agonist L 775 606.
View Article and Find Full Text PDFTandem hydroformylation/Fischer indole synthesis: a novel and convenient approach to indoles from olefins.
Org Lett
September 2003
Fachbereich Chemie, Organische Chemie I, Universität Dortmund, Otto-Hahn-Str. 6, 44227 Dortmund.
[reaction: see text] A novel one-pot synthesis of indole systems via tandem hydroformylation/Fischer indole synthesis starting from olefins and arylhydrazines is described. This tandem procedure leads directly to 3-substituted indoles if unsubstituted phenylhydrazine is used and to 3,5- respectively 3,7-disubstituted indoles if para- or ortho-substituted arylhydrazines are used.
View Article and Find Full Text PDF