Simple indole alkaloids and those with a nonrearranged monoterpenoid unit

Ishikura, Minoru; Yamada, Koji

doi:10.1039/b820693g

Cited by 115 publications

(24 citation statements)

References 226 publications

(218 reference statements)

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“…4, 182.2, 140.5, 136.3, 135.0, 130.9, 129.6, 129.31, 129.29, 128.6, 128.3, 128.2, 127.7, 126.2, 114.0, 113.5, 107.0, 44.9, 44.5, 40.8, 34. 1 H NMR (400 MHz, CDCl 3 ): δ = 16.44 (s, 1 H), 7.48 (t, J = 6.9 Hz, 2 H), 7 H),7.16 (t,J = 7.3 Hz,2 H),6.41 (dd,J = 3.1,1.8 Hz,1 H),6.21 (d,1 H),4.66 (s,1 H),3.53 (dd,J = 11.7,6.4 Hz,1 H),3.27 (dd,J = 19.7,11.8 Hz,1 H),3.06 (dd,J = 19.7,6.4 Hz, 1 H). 13 C NMR (100 MHz, CDCl 3 ) : δ = 195.3, 183.6, 149.3, 144.2, 136.1, 135.1, 131.0, 129.6, 129.3, 128.6, 128.3, 126.2, 113.7, 113.1, 112.4, 111.2, 103.7, 43.7, 43.5, 41.6, 34.9 7.46-7.37 (m, 5 H), 7.37-7.27 (m, 5 H), 7.02 (d, J = 7.4 Hz, 2 H), 4.57 (s, 1 H), 3.44-3.30 (m, 2 H), 3.21-3.08 (m, 1 H). 13 C NMR (125 MHz, CDCl 3 ) : δ = 197.0, 181.8, 150.9, 150.4, 137.7, 136.4, 134.4, 132.0, 130.9, 129.8, 129.4, 128.6, 128.3, 125.8, 123.5, 114.0, 112.9, 104.4, 47.1, 44.1, 40.4, 34.4 = 196.9, 180.9, 168.1, 136.5, 136.3, 134.9, 133.5, 132.6, 130.5, 129.5, 129.2, 129.1, 128.9, 128.3, 128.1, 125.7, 124.3, 119.1, 117.3, 116.3, 114.1, 113.6, 105.4, 44.5, 41.9, 41.4, 34.4.…”

Section: One-pot Procedures For 3aamentioning

confidence: 99%

“…13 C NMR (100 MHz, CDCl 3 ) : δ = 195.3, 183.6, 149.3, 144.2, 136.1, 135.1, 131.0, 129.6, 129.3, 128.6, 128.3, 126.2, 113.7, 113.1, 112.4, 111.2, 103.7, 43.7, 43.5, 41.6, 34.9 7.46-7.37 (m, 5 H), 7.37-7.27 (m, 5 H), 7.02 (d, J = 7.4 Hz, 2 H), 4.57 (s, 1 H), 3.44-3.30 (m, 2 H), 3.21-3.08 (m, 1 H). 13 C NMR (125 MHz, CDCl 3 ) : δ = 197.0, 181.8, 150.9, 150.4, 137.7, 136.4, 134.4, 132.0, 130.9, 129.8, 129.4, 128.6, 128.3, 125.8, 123.5, 114.0, 112.9, 104.4, 47.1, 44.1, 40.4, 34.4 = 196.9, 180.9, 168.1, 136.5, 136.3, 134.9, 133.5, 132.6, 130.5, 129.5, 129.2, 129.1, 128.9, 128.3, 128.1, 125.7, 124.3, 119.1, 117.3, 116.3, 114.1, 113.6, 105.4, 44.5, 41.9, 41.4, 34.4. 15 (s,1 H),7.99 (d,J = 8.4 Hz,1 H),7.77 (d,J = 8.4 Hz,2 H),7.45 (s,1 H),4 H),7.25 (d,J = 8.5 Hz,4 H),3 H),6.94 (t,J = 7.9 Hz, 2 H), 6.76 (d, J = 7.2 Hz, 2 H), 4.82 (s,1 H),3.56 (dd,J = 11.8,6.0 Hz,1 H),3.34 (dd,J = 19.7,11.9 Hz,1 H),3.11 (dd,J = 19.7,6.0 Hz, 1 H), 2.34 (s, 3 H).…”

Section: One-pot Procedures For 3aamentioning

confidence: 99%

“…4, 182.7, 137.1, 135.8, 134.9, 134.8, 130.2, 129.54, 129.48, 129.3, 129.0, 128.7, 128.3, 127.7, 114.3, 113.0, 105.4, 49.1, 44.4, 40.2, 34.7 (dd,J = 19.7,11.7 Hz,1 H),3.11 (dd,J = 19.7,6.3 Hz, 1 H). 13 C NMR (100 MHz, CDCl 3 ): δ = 195. 4, 182.7, 135.8, 135.2, 134.8, 131.6, 130.2, 129.52, 129.47, 129.2, 129.0, 128.3, 127.8, 125.4, 114.3, 113.0, 105.4, 49.0, 44.3, 40.2, 34.7.…”

Section: Papermentioning

confidence: 99%

“…Syn thesis 13 C NMR (100 MHz, CDCl 3 ): δ = 193. 7, 184.3, 136.6, 135.4, 131.2, 129.6, 129.4, 128.9, 128.2, 127.6, 114.6, 114.2, 105.0, 47.7, 43.9, 40.8, 35.3, 32.4, 24.0, 21.8 4, 192.9, 135.3, 134.7, 134.3, 129.9, 129.5, 129.09, 129.07, 128.8, 115.8, 113.8, 61.6, 53.8, 46.5, 41.2, 40.1, 36.2, 28. = 191.7, 188.5, 158.9, 152.7, 152.1, 135.4, 135.2, 134.0, 130.2, 129.4, 129.1, 128.9, 128.5, 126.8, 126.0, 125.3, 120.3, 117.2, 116.6, 113.9, 112.9, 102.0, 44.9, 43.4, 43.1, 36.8 7.46-7.36 (m, 6 H), 7.34-7.29 (m, 4 H), 7.28-7.24 (m, 2 H), 7.16 (t, J = 3.7 Hz, 2 H), 4.46 (s,1 H),3.46 (dd,J = 11.6,6.2 Hz,1 H),3.32 (dd,J = 20.0,11.4 Hz,1 H),3.12 (dd,J = 19.6,6.4 Hz, 1 H).…”

Section: Papermentioning

confidence: 99%

“…[13][14][15] Molecules containing these scaffolds exhibit a broad range of bioactivity, therefore, they were also used in our method to expand the library of 3. Remarkably, indoleand coumarin-substituted methylenemalononitriles were used successfully in the reaction to give 3aal, 3aam, and 3aap in 60-66 % yields (entries 12, 13, and 16); these compounds have a high possibility of having interesting bioactivity.…”

Section: Paper Syn Thesismentioning

confidence: 99%

See 4 more Smart Citations

Base-Catalyzed Domino Double Michael Reactions of 1-Hydroxy-1,4-dien-3-ones and 2-Alkylidenemalononitriles: A Diastereoselective Route to Polysubstituted 3-Alkanoyl-4-hydroxycyclohex-3-enes

et al. 2014

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The diastereoselective synthesis of 2,6-disubstituted 3-alkanoyl-4-hydroxycyclohex-3-ene-1,1-dicarbonitriles has been developed through domino double Michael addition of 1,5-disubstituted 1-hydroxy-1,4-dien-3-ones to 2-alkylidenemalononitriles catalyzed by triethylamine. This simple domino process affords a variety of highly functionalized 3-alkanoyl-4-hydroxycyclohex-3-enes, some of which are not easily accessible using other methodologies, in moderate to good yields and excellent diastereoselectivity (dr > 95:5). Thus, the generality of this process and feasibility of introducing bioactive moieties make this reaction highly valuable in synthetic and medicinal chemistry. Key words domino reaction, Michael addition, diastereoselectivity, cyclohexanone, curcuminThe construction of suitably functionalized cyclohexanones and related cyclohexanol skeletons plays a central role in many natural product syntheses due to their significant biological and pharmaceutical importance. 1 In literature reports, many methods for the synthesis of substituted cyclohexanones have arisen from different approaches, such as [4+2] cycloaddition, 2 rhodium(I)-catalyzed PausonKhand reaction, 3 palladium-catalyzed intramolecular hydroalkylation, 4 organocatalyzed domino annulation, 5 and reductive tandem double Michael cascade, 6a highlighting the continued interest in these frameworks from the synthetic community. In particular, domino processes are a powerful strategy for the construction of complex molecular skeletons by simultaneous formation of two or more bonds from simple materials in a one-pot manner. 7 These benefits are of particular interest in pharmaceutical research for the construction of libraries of biologically active compounds. Therefore, developing novel domino reactions for the preparation of structurally diverse chemical libraries of polyfunctional compounds remains an interest for synthetic chemists. In this field, the usefulness of sequential Michael additions has been demonstrated, 8 and domino Michael reactions have especially emerged as one of the most potent tools for the synthesis of various important cyclic building blocks during recent decades.It is well documented that the Michael reaction of chalcones containing an activated alkene, such as nitroolefins and 1,5-disubstituted penta-1,4-dien-3-ones, with active methylene substrates, such as malononitrile and 1,3-dicarbonyl compounds, can be employed to prepare highly substituted cyclohexanones, while chalcones can serve both as the starting Michael donor and ending acceptor in domino double Michael reactions (Scheme 1, type 1) and bischalcones as the Michael acceptors twice in the reaction course (type 2). Recently, curcumin and its derivatives, also bischalcones, are reported to have chalcone-like behavior and they have been used to build substituted cyclohexanones with nitroolefins and chalcones (type 3). 6b,c Although, there are several reports of the use of δ-aryl-β-oxo-γ,δ-unsaturated esters, 9 to the best of our knowledge there are no reports...

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Section: One-pot Procedures For 3aamentioning

confidence: 99%

Section: One-pot Procedures For 3aamentioning

confidence: 99%

Section: Papermentioning

confidence: 99%

Section: Papermentioning

confidence: 99%

Section: Paper Syn Thesismentioning

confidence: 99%

See 3 more Smart Citations

Base-Catalyzed Domino Double Michael Reactions of 1-Hydroxy-1,4-dien-3-ones and 2-Alkylidenemalononitriles: A Diastereoselective Route to Polysubstituted 3-Alkanoyl-4-hydroxycyclohex-3-enes

et al. 2014

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Gold‐catalyzed Rapid Construction of Nitrogen‐containing Heterocyclic Compound Library with Scaffold Diversity and Molecular Complexity

Jin

Jia

et al. 2019

Adv Synth Catal

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1,3-unsubstituted 2-(1H-indol-2-yl)ethanamines were employed for the first time to react with alkynoic acids (AAs) to achieve gold-catalyzed highly selective cascade reactions to furnish novel indole-fused skeletons. Furthermore, with this powerful gold catalytic system, a library of indole/pyrrole/thiophene/benzene/naphthalene/ pyridine-based nitrogen-containing heterocyclic compounds (NCHCs) with scaffold diversity and molecular complexity was constructed rapidly using various amine nucleophiles (ANs) and diverse AAs as the building blocks. This general protocol features excellent selectivity, extraordinarily broad substrate scope, readily available inputs, good to high yields, high bond-forming efficiency, and step economy, thus providing a facile and efficient access to a variety of valuable nitrogen-containing heterocycles. LRMS (ESI) m/z: 218 [M + H] + ; HRMS (ESI) m/z calculated for C 12 H 11 NO 3 + H + 218.0812, found: 218.0809. 2 3 4 5 6 7 8

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Recent Developments in Photo‐Catalyzed/Promoted Synthesis of Indoles and Their Functionalization: Reactions and Mechanisms

2020

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The use of clean and renewable light sources is increasingly common in organic synthesis due to its safety, practicality and economy. Recently, photoredox catalysis has shown great application values in organic transformations because of its advantages of environmentally friendly and abundant resources. Indoles and their derivatives (indolines, oxindoles and isatins) are the core skeletons of some important organic compounds and widely‐present in various natural products and pharmaceuticals with different biological activities. Therefore, the research on the synthesis and modification of indoles is particularly important for chemists and pharmacologists. This review summarizes the effects of photocatalysis on indole synthesis and modification in recent decades. These transformations are accomplished by using metal photocatalysts (i. e., Ir, Ru, Ni, Cu, Fe, Au, Rh, TiO2, etc.) or non‐metallic photocatalysts (i. e., Rose Bengal, Eosin Y, quinones, naphthols, N‐heterocyclic carbenes, carbazoles, pyrylium salts, etc.), or without the need of photocatalysts. The detailed mechanisms of these photo‐catalyzed/promoted organic reactions are also highlighted deeply. And we hope this review will be helpful to researchers interested in this promising field of photocatalyzed transformations.

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Simple indole alkaloids and those with a nonrearranged monoterpenoid unit

Cited by 115 publications

References 226 publications

Base-Catalyzed Domino Double Michael Reactions of 1-Hydroxy-1,4-dien-3-ones and 2-Alkylidenemalononitriles: A Diastereoselective Route to Polysubstituted 3-Alkanoyl-4-hydroxycyclohex-3-enes

Base-Catalyzed Domino Double Michael Reactions of 1-Hydroxy-1,4-dien-3-ones and 2-Alkylidenemalononitriles: A Diastereoselective Route to Polysubstituted 3-Alkanoyl-4-hydroxycyclohex-3-enes

Gold‐catalyzed Rapid Construction of Nitrogen‐containing Heterocyclic Compound Library with Scaffold Diversity and Molecular Complexity

Recent Developments in Photo‐Catalyzed/Promoted Synthesis of Indoles and Their Functionalization: Reactions and Mechanisms

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