- One-pot, three-component Fischer indolisation-N-alkylation for rapid synthesis of 1,2,3-trisubstituted indoles
-
A one-pot, three-component protocol for the synthesis of 1,2,3-trisubstituted indoles has been developed, based upon a Fischer indolisation-indoleN-alkylation sequence. This procedure is very rapid (total reaction time under 30 minutes), operationally straightforward, generally high yielding and draws upon readily available building blocks (aryl hydrazines, ketones, alkyl halides) to generate densely substituted indole products. We have demonstrated the utility of this process in the synthesis of 23 indoles, benzoindoles and tetrahydrocarbazoles bearing varied and useful functionality.
- Hughes-Whiffing, Christopher A.,Perry, Alexis
-
supporting information
p. 627 - 634
(2021/02/06)
-
- Synthesis of 3,3′-Disubstituted Indolenines Utilizing the Lewis Acid Catalyzed Alkylation of 2,3-Disubstituted Indoles with Trichloroacetimidates
-
Trichloroacetimidates function as effective electrophiles for the selective C3-alkylation of 2,3-disubstituted indoles to provide 3,3′-disubstituted indolenines. These indolenines are common synthetic intermediates that are often utilized in the synthesis of complex molecules. Effective reaction conditions utilizing Lewis acid catalysts have been determined, and the scope of the reaction with respect to indole and imidate reaction partner has been investigated. This chemistry provides an alternative to base promoted and transition-metal-catalyzed methods that are more commonly utilized to access similar indolenines.
- Adhikari, Arijit A.,Radal, Léa,Chisholm, John D.
-
supporting information
p. 2335 - 2339
(2017/10/06)
-
- Palladium-catalyzed decarboxylative allylation and benzylation of N-alloc and N-Cbz indoles
-
A set of general methods for the palladium-catalyzed decarboxylative C3-allylation and C3-benzylation of indoles, starting from the corresponding N-alloc and N-Cbz indoles, respectively, is reported. This chemistry provides ready access to a wide range of
- Montgomery, Thomas D.,Zhu, Ye,Kagawa, Natsuko,Rawal, Viresh H.
-
supporting information
p. 1140 - 1143
(2013/03/29)
-
- N-indolyltriethylborate: A useful reagent for synthesis of C3-quaternary indolenines
-
N-Indolyltriethylborate was found to be a useful reagent for dearomatizing C3-alkylation of 3-substituted indoles with both activated and nonactivated alkyl halides to give C3-quaternary indolenines, pyrroloindolines, furoindoline, and hexahydropyridoindoline under mild reaction conditions. The utility of these reagents was demonstrated in the syntheses of a pyrroloindoline-4- cholestene hybrid and debromoflustramine B.
- Lin, Aijun,Yang, Jiong,Hashim, Mohamed
-
supporting information
p. 1950 - 1953
(2013/06/04)
-
- Palladium-catalyzed C3-benzylation of indoles
-
A general method for regioselective C3-benzylation of indoles has been developed. Various 3-substituted indoles and benzyl methyl carbonates with different electronic properties react under mild conditions to afford a diverse range of 3-benzylindolenine products in good yields.
- Zhu, Ye,Rawal, Viresh H.
-
supporting information; experimental part
p. 111 - 114
(2012/03/07)
-
- Ring transformations of heterocyclic compounds. XXII [1]. Pyrido[1,2-a]indolium salts from 2-methyl-3H-indoles by pyrylium mediated three carbon annelation
-
The synthesis of pyrido[1,2-a]indolium perchlorates 8,11 from 2,4,6-triarylpyrylium perchlorates 1 and 2-methyl-3H-indoles 6,9 in the presence of a basic condensing agent (anhydrous sodium acetate, piperidine acetate, triethylamine/acetic acid, triethylamine) in ethanol by a 2,4-[C3+C2N] pyrylium ring transformation is reported. Spectroscopic data of the transformation products and their mode of formation are discussed.
- Zimmermann, Thomas,Hennig, Lothar
-
p. 263 - 269
(2007/10/03)
-