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Review
. 2024 Oct 22;29(21):4997.
doi: 10.3390/molecules29214997.

Synthesis and Biological Activity of Chromeno[3,2- c]Pyridines

Anna V Listratova  1 , Roman S Borisov  2 , Nikolay Yu Polovkov  2 , Larisa N Kulikova  1
Affiliations
Review

Synthesis and Biological Activity of Chromeno[3,2- c]Pyridines

Anna V Listratova et al. Molecules. .

Abstract

The review summarizes all synthetic methodologies for the preparation of chromeno[3,2-c]pyridines and chromeno[3,2-c]quinolines. The proposed approaches are systemized based on ways for the construction of the heterocyclic system. The presence of these compounds in nature and their bioactivity are also discussed. Natural products with an annelated chromeno[3,2-c]pyridine fragment are well-known and a number of alkaloids derived from this system as a key core have been recently isolated. These compounds demonstrate antimicrobial, antivirus, and cytotoxic activities, making chromeno[3,2-c]pyridine structural motifs promising for medicinal chemistry.

Keywords: biological activities; chromeno[3,2-c]pyridines; chromeno[3,2-c]quinolines; chromenopyridines; synthesis.

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Conflict of interest statement

The authors declare no conflicts of interest.

Figures

Figure 1
Figure 1
Natural chromeno[3,2-c]pyridines.
Scheme 1
Scheme 1
A proposed the biosynthetic pathway towards chromeno[3,2-c]pyridine moiety.
Figure 2
Figure 2
Natural chromeno[3,2-c]pyridine.
Figure 3
Figure 3
Natural chromeno[3,2-c]pyridines.
Scheme 2
Scheme 2
The first suggested synthetic ways towards chromeno[3,2-c]pyridines.
Scheme 3
Scheme 3
Synthesis of chromeno[3,2-c]quinolines 17.
Scheme 4
Scheme 4
Cyclisation of 4-phenoxynicotinic acid 20 towards chromeno[3,2-c]pyridine 14.
Scheme 5
Scheme 5
Synthesis of chromeno[3,2-c]quinolines 24.
Scheme 6
Scheme 6
Cyclisation of 3-trifluoroacetyl-4-quinolyl ethers 26.
Scheme 7
Scheme 7
An efficient method to chromeno[3,2-c]quinolines 31.
Scheme 8
Scheme 8
Synthesis of chromeno[3,2-c]quinolines 33 and 34.
Scheme 9
Scheme 9
Synthesis of chromeno[3,2-c]pyridine 39.
Scheme 10
Scheme 10
A construction of chromeno[3,2-c]pyridine core based on condensation of morpholine enamine and salicylaldehyde.
Scheme 11
Scheme 11
Synthesis of chromeno[3,2-c]pyridine 14 starting form β-ketoester 45.
Scheme 12
Scheme 12
Synthesis of a series of chromeno[3,2-c]pyridines via condensation of enamines 48 and salisylaldehydes 49.
Scheme 13
Scheme 13
Synthesis of dye 57.
Scheme 14
Scheme 14
Synthesis of chromeno[3,2-c]pyridine 14 via nucleophilic substitution.
Scheme 15
Scheme 15
Intramolecular cyclization of (2-chlorophenyl)(2-methoxypyridin-3-yl)methanone 60.
Scheme 16
Scheme 16
Synthesis of a series of chromeno[3,2-c]pyridines 62 from chromene-3-thiocarboxamides 61.
Scheme 17
Scheme 17
Synthesis of chromeno[3,2-c]pyridine 67.
Scheme 18
Scheme 18
Michael addition/intramolecular O-cyclization/elimination cascade.
Scheme 19
Scheme 19
An efficient method for the synthesis of chromeno[3,2-c]quinolones 77.
Scheme 20
Scheme 20
One-pot three-component synthesis towards chromeno[3,2-c]pyridines 81.
Scheme 21
Scheme 21
The synthesis of benzo[5,6]chromeno[3,2-c]quinolones 83.
Scheme 22
Scheme 22
Synthesis of chromeno[3,2-c]quinolones 87 and 88.
Scheme 23
Scheme 23
Synthesis of a series of chromeno[3,2-c]pyridines 92.
Scheme 24
Scheme 24
Synthesis of chromenopyridines from 2-(2-dimethylaminoethenyl)chromones 95.
Scheme 25
Scheme 25
Use of chromones 101 in construction of chromeno[3,2-c]pyridine core.
Scheme 26
Scheme 26
Synthesis of fluorescent chromeno[3,2-c]pyridines 107 and 108.
Scheme 27
Scheme 27
A TMSCl-promoted cyclization of 3-formylchromone with various anilines 110.
Scheme 28
Scheme 28
Synthesis of chromeno[3,2-c]pyridines 114 via 5+3] cycloaddition.
Scheme 29
Scheme 29
Intramolecular C-arylation in Ugi adduct chromones 119.
Scheme 30
Scheme 30
Synthesis of a series of chromeno[3,2-c]pyridines 124.
Scheme 31
Scheme 31
[4+2]-cycloaddition in the construction of the chromeno[3,2-c]pyridines 129 (A) and 131 (B).
Scheme 32
Scheme 32
Synthesis of thiophene-fused chromeno[3,2-c]pyridine 134.
Scheme 33
Scheme 33
Synthesis of chromeno[3,2-c]pyridines 138 via a domino three-component reaction.
Scheme 34
Scheme 34
An acid-promoted cascade cyclization of aryl group-substituted propargyl alcohol derivatives 139.
Scheme 35
Scheme 35
Pd(II)-catalyzed tandem C–H alkenylation/C–O cyclization in the synthesis of chromeno[3,2-c]quinoline 142.
Scheme 36
Scheme 36
Synthesis of chromenopyridodiazepinone 144 with chromeno[3,2-c]pyridine moiety.
Scheme 37
Scheme 37
Synthesis of chromeno[3,2-c]quinolones 147 via a FeIII-catalyzed imine formation/C-C coupling/oxidation cascade.
Scheme 38
Scheme 38
Stereochemistry in the synthesis of hexahydrochromenopyridines 150 and 151.
Scheme 39
Scheme 39
Synthesis of chromeno[3,2-c]pyridines 154.
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