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. 2019 Mar 14;9(15):8369-8372.
doi: 10.1039/c9ra00995g. eCollection 2019 Mar 12.

1-Alkyl-3-alkylindolin-2-imine hydrochlorides as useful building blocks in the copper-catalyzed synthesis of polycyclic indoline scaffolds

Can Liu  1   2 , Haijun Yang  2 , Changjin Zhu  1 , Hua Fu  1   2
Affiliations

1-Alkyl-3-alkylindolin-2-imine hydrochlorides as useful building blocks in the copper-catalyzed synthesis of polycyclic indoline scaffolds

Can Liu et al. RSC Adv. .

Abstract

A novel and efficient copper-catalyzed synthesis of dihydro-6H-indolo[2,3-b]quinoline derivatives has been developed by using 3-alkyl-1-alkylindolin-2-imine hydrochlorides as the building blocks. Furthermore, easy reduction of dihydro-6H-indolo[2,3-b]quinolines with diisobutylaluminum hydride provided tetrahydro-6H-indolo[2,3-b]quinoline derivatives in excellent yields. The present method shows some advantages including use of cheap cuprous chloride as the catalyst and tolerance of wide functional groups.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Fig. 1
Fig. 1. Structures of representative perophoramidine and communesin alkaloids with diverse biological activities.
Scheme 1
Scheme 1. Synthesis of polycyclic indoline scaffolds using tryptamine derivatives (a) or 1-alkyl-3-alkylindolin-2-imine hydrochlorides (b) as the useful building blocks.
Scheme 2
Scheme 2. (a) Reaction of 3-benzyl-1-methylindolin-2-imine hydrochloride (1g) with 2-iodobenzyl bromide (2a) in the absence of copper catalyst leading to 4. (b) Copper-catalyzed intramolecular cyclization of 4 under the standard conditions.
Scheme 3
Scheme 3. Reaction mechanism for the copper-catalyzed synthesis of dihydro-6H-indolo[2,3-b]quinolines (3).
Scheme 4
Scheme 4. Reduction of dihydro-6H-indolo[2,3-b]quinolines (3) with DIBAL-H leading to tetrahydro-6H-indolo[2,3-b]quinolines (5).
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