coumarin(2H-Chromen-2-one),Aka1,2-Benzopyranone,Secondary metabolites widely distributed in the plant kingdom,Often close to studentsCinnamic acid\Flavonoids\LignansIsogenesis,Widely distributed in higher plants,Especially Umbelliferae\Rutaceae\Compositae\Leguminosae\Orchidaceae\Solanaceae\Daphneideraceae\Among the metabolites of plants and microorganisms such as Saxifragaceae and Melilotus.Coumarin under UV light\Visible light and when encountering concentrated sulfuric acid,Can produce blue fluorescence;It can regulate plant growth\Antibacterial and antiviral\Anticoagulant \smooth muscle relaxation \Various biological activities such as UV absorption and radiation resistance.So far, many coumarins have been isolated from citrus plants in Rutaceae.
Synthetic Circuit 1
1.1
Catalysts:
Potassium hydroxide
,
Bismuth silver carbonate oxide (Bi0.88Ag0.17(CO3)O2)
Solvents:
Dimethylformamide
;
24 h, 110 °C
Reference
Exploiting a silver-bismuth hybrid material as heterogeneous noble metal catalyst for decarboxylations and decarboxylative deuterations of carboxylic acids under batch and continuous flow conditions
Meszaros, Rebeka; et al,
Green Chemistry,
2021,
23(13),
4685-4696
Synthetic Circuit 2
1.1
Solvents:
Pyridine
;
5 h, heated
1.2
Reagents:
Hydrochloric acid
Solvents:
Water
;
acidified, 0 °C
Reference
Some unusual reactions of Meldrum's acid. Synthesis of cinnamic acids, coumarins and 2-benzyl-1-indanone
Mahulikar, P. P.; et al,
Journal of Chemical Research,
2006,
(1),
12-14
Synthetic Circuit 3
1.1
Reagents:
1,3-Dibromo-5,5-dimethylhydantoin
,
Water
,
Pyridine, hydrofluoride (1:9)
Solvents:
Dichloromethane
Reference
Fluorination studies using difluoroiodotoluene
Greaney, Michael Francis,
1999,
,
,
Synthetic Circuit 4
1.1
Reagents:
1,1′-Carbonyldiimidazole
,
Water
Solvents:
Anisole
;
5 min, rt
1.2
Catalysts:
Dabco
;
48 h, rt
Reference
A water-promoted catalytic hydrodecarboxylation of conjugated carboxylic acids under open air conditions at room temperature
Wang, Zhan-Yong; et al,
Green Chemistry,
2023,
25(8),
3040-3045
Synthetic Circuit 5
1.1
Solvents:
Acetonitrile
;
27 h, rt
Reference
Combinatorial discovery of two-photon photoremovable protecting groups
Pirrung, Michael C.; et al,
Proceedings of the National Academy of Sciences of the United States of America,
2003,
100(22),
12548-12553
Synthetic Circuit 6
1.1
Reagents:
Cuprous chloride
Solvents:
Acetonitrile
1.2
Reagents:
Sodium hydroxide
Solvents:
Water
Reference
Thiocarbonyl to carbonyl group transformation using cuprous chloride and sodium hydroxide
Narasimhamurthy, N.; et al,
Tetrahedron Letters,
1986,
27(33),
3911-12
Synthetic Circuit 7
1.1
Catalysts:
Di-μ-chlorotetrakis(2-phenylpyridine)diiridium
Solvents:
Acetonitrile
;
36 h, rt
Reference
Synthesis of (Z)-Cinnamate Derivatives via Visible-Light-Driven E-to-Z Isomerization
Shu, Penghua; et al,
SynOpen,
2019,
3(4),
103-107
Synthetic Circuit 8
1.1
Reagents:
Benzoyl peroxide
,
N-Bromosuccinimide
Solvents:
Carbon tetrachloride
;
2 h, reflux; reflux → 0 °C
1.2
Reagents:
Sodium carbonate
Solvents:
Water
;
0 °C
Reference
Aromatization of Stobbe reaction products
Jabbar, Saba; et al,
Asian Journal of Chemistry,
2002,
14(3-4),
1799-1800
Synthetic Circuit 9
1.1
Reagents:
Potassium carbonate
Solvents:
Dimethylformamide
;
rt → 140 °C
1.2
Catalysts:
(SP-4-1)-Dichlorobis[1-(dicyclohexylphosphino-κP)piperidine]palladium
Solvents:
Tetrahydrofuran
;
24 h, 140 °C; 140 °C → rt
1.3
Reagents:
Hydrochloric acid
Solvents:
Water
;
rt
Reference
Mizoroki-Heck Reactions Catalyzed by Dichloro{bis[1-(dicyclohexylphosphanyl)piperidine]}palladium: Palladium Nanoparticle Formation Promoted by (Water-Induced) Ligand Degradation
Oberholzer, Miriam; et al,
Advanced Synthesis & Catalysis,
2012,
354(4),
627-641
Synthetic Circuit 10
1.1
Solvents:
Ethanol
;
rt
Reference
Photoconversion of o-hydroxycinnamates to coumarins and its application to fluorescence imaging
Cho, Sung-Youl; et al,
Tetrahedron Letters,
2009,
50(33),
4769-4772
Synthetic Circuit 11
Reference
Photocyclization reactions. Part 8. Synthesis of 2-quinolone, quinoline, and coumarin derivatives using trans-cis isomerization by photoreaction
Horaguchi, Takaaki; et al,
Journal of Heterocyclic Chemistry,
2002,
39(1),
61-67
Synthetic Circuit 12
1.1
Catalysts:
Potassium carbonate
,
Tetrabutylammonium bromide
;
1 h, 135 - 140 °C; 6 h, 135 - 140 °C
1.2
Reagents:
Sodium carbonate
Solvents:
Water
;
pH 8, rt
Reference
Design, synthesis, antifungal activity, and 3D-QSAR of coumarin derivatives
Wei, Yan; et al,
Journal of Pesticide Science (Tokyo,
2018,
43(2),
88-95
Synthetic Circuit 13
1.1
Catalysts:
Grubbs second generation catalyst
Solvents:
Dichloromethane
;
24 h, 45 °C
Reference
Aldehyde-Assisted Ruthenium(II)-Catalyzed C-H Oxygenations
Yang, Fanzhi; et al,
Angewandte Chemie,
2014,
53(42),
11285-11288
Synthetic Circuit 14
1.1
Catalysts:
Grubbs second generation catalyst
Solvents:
Dichloromethane
;
overnight, rt
Reference
Simple synthesis of versatile coumarin scaffolds
Lay, Luigi,
Synthetic Communications,
2006,
36(15),
2203-2209