- Extended Multicomponent Reactions with Indole Aldehydes: Access to Unprecedented Polyheterocyclic Scaffolds, Ligands of the Aryl Hydrocarbon Receptor
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The participation of reactants undergoing a polarity inversion along a multicomponent reaction allows the continuation of the transformation with productive domino processes. Thus, indole aldehydes in Groebke–Blackburn–Bienaymé reactions lead to an initial adduct which spontaneously triggers a series of events leading to the discovery of novel reaction pathways together with direct access to a variety of linked, fused, and bridged polyheterocyclic scaffolds. Indole 3- and 4-carbaldehydes with suitable isocyanides and aminoazines afford fused adducts through oxidative Pictet–Spengler processes, whereas indole 2-carbaldehyde yields linked indolocarbazoles under mild conditions, and a bridged macrocycle at high temperature. These novel structures are potent activators of the human aryl hydrocarbon receptor signaling pathway.
- Ghashghaei, Ouldouz,Pedrola, Marina,Seghetti, Francesca,Martin, Victor V.,Zavarce, Ricardo,Babiak, Michal,Novacek, Jiri,Hartung, Frederick,Rolfes, Katharina M.,Haarmann-Stemmann, Thomas,Lavilla, Rodolfo
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supporting information
p. 2603 - 2608
(2020/11/30)
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- An efficient one-pot synthesis of 2-benzylpyrroles and 3-benzylindoles
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One-pot regioselective benzylation of pyrroles and indoles using zirconium tetrachloride is discussed. This has been achieved by in-situ generation of di(1H-pyrrol-1-yl)zirconium(IV) chloride and di(1H-indol-1-yl)zirconium(IV) chloride. It was observed th
- Sharma, Ratnesh,Chouhan, Mangilal,Sood, Divya,Nair, Vipin A.
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experimental part
p. 305 - 309
(2012/01/03)
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- In Situ vinylpyrrole synthesis. Diels-alder reactions with maleimides to give tetrahydroindoles
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(Chemical Equation Presented) A series of 108 tetrahydroindoles has been prepared by a one-pot synthesis from 2-alkylpyrroles, cyclic ketones, maleimides, and an acid catalyst. A 5-vinylpyrrole is formed by an acid-catalyzed condensation of a 2-alkyl-substituted pyrrole with a ketone, which is subsequently trapped in situ by a maleimide in a predominantly endo-addition Diels-Alder reaction. Isomerization of the double bond into the pyrrole ring gives a tetrahydroindole with predominant cis-fusion of the cycloalkane ring.
- Noland, Wayland E.,Lanzatella, Nicholas P.,Sizova, Elena P.,Venkatraman, Lakshmanan,Afanasyev, Oleg V.
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scheme or table
p. 503 - 534
(2009/09/05)
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- A General Method for the Preparation of 2-Benzylpyrroles by Modified Borohydride Reduction of Azafulvenium Salts
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2-Benzylpyrroles (5a-h) can be prepared in high yield from pyrroles by reduction, with modified borohydride reagents, of the corresponding 1-azafulvenium salts (3a-h) generated in situ in the presence of excess of phosphoryl trichloride.The procedure is compatible with ester groups.
- McGillivray, George,Smal, Elma
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p. 633 - 636
(2007/10/02)
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- Tandem Alkylation-Reduction of 2-Acylpyrroles. Convenient One-Pot Syntheses of 2-Benzylpyrroles
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Tandem alkylation-reduction of 2-acylpyrroles is described for the convenient one-pot syntheses of 2-benzylpyrroles.By this convenient procedure 2-(p-methoxybenzyl)pyrrole (2), 2-benzylpyrrole (3), 2-(p-methylbenzyl)pyrrole (4), 2-(o-methoxybenzyl)pyrrole
- Schumacher, Doris P.,Hall, Stan S.
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p. 5060 - 5064
(2007/10/02)
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