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. 2018 Nov 22:14:2907-2915.
doi: 10.3762/bjoc.14.269. eCollection 2018.

Synthesis of indole-cycloalkyl[ b]pyridine hybrids via a four-component six-step tandem process

Muthumani Muthu  1 , Rakkappan Vishnu Priya  2 , Abdulrahman I Almansour  3 , Raju Suresh Kumar  3 , Raju Ranjith Kumar  1
Affiliations

Synthesis of indole-cycloalkyl[ b]pyridine hybrids via a four-component six-step tandem process

Muthumani Muthu et al. Beilstein J Org Chem. .

Abstract

The one-pot four-component reaction of 3-(1H-indol-3-yl)-3-oxopropanenitriles, aromatic aldehydes, cycloalkanones and ammonium acetate occurred via a six-step tandem Knoevenagel condensation-nucleophilic addition to carbonyl-Michael addition-N-cyclization-elimination-air oxidation sequence to afford structurally intriguing indole-cycloalkyl[b]pyridine-3-carbonitrile hybrid heterocycles in excellent yields.

Keywords: 3-(1H-indol-3-yl)-3-oxopropanenitrile; cycloalkyl[b]pyridine-3-carbonitrile; cyclododecanone; tandem reaction.

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Figures

Figure 1
Figure 1
Examples of biologically important cycloalkyl-fused pyridines.
Scheme 1
Scheme 1
Synthesis of 3-oxopropanenitriles 3.
Scheme 2
Scheme 2
Proposed mechanism for the formation of 7f.
Scheme 3
Scheme 3
Synthesis of indole–cyclododeca[b]pyridine-3-carbonitriles 7 and 14.
Figure 2
Figure 2
Axial chirality due to restricted C–C bond rotation (representative cases).
Figure 3
Figure 3
ORTEP diagram of 12r.
Scheme 4
Scheme 4
Synthesis of indole–cycloalkyl[b]pyridine-3-carbonitrile hybrids 15–18.
Figure 4
Figure 4
ORTEP diagram of 16f.
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