Metal-free synthesis of polysubstituted pyrroles using surfactants in aqueous medium

Kumar, Amrendra; Rāmānand,; Narender, Tadigoppula

doi:10.1039/c7gc01874f

Cited by 18 publications

(8 citation statements)

References 53 publications

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“…Thermlupine E (5) had a molecular formula C 17 H 18 N 2 O 3 , as determined by its HRESIMS spectrum (m/z 321.1198 [M + Na] + , calcd for 321.1210). The NMR data of 5 were similar to those of cytisine ( 24), 20 24 The absolute configuration of 5 was established as 7R, 9S based on the biosynthetic pathway and NMR data analysis, which was verified through ECD calculations (Figure S3). Thermlupine F (6) was assigned the molecular formula C 15 H 22 N 2 O based on the HRESIMS spectrum (m/z 269.1631 [M + Na] + , calcd for 269.1624).…”

Section: Journal Of Agricultural Andsupporting

confidence: 55%

Quinolizidine Alkaloids and Isoflavones from the Herb of Thermopsis lupinoides and Their Antiviral, Antifungal, and Insecticidal Activities

Zhang,

Tian,

Zhang

et al. 2024

J. Agric. Food Chem.

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As part of our ongoing investigation of natural bioactive substances from the genus Thermopsis of the tribe Fabaceae for agricultural protection, the chemical constituents of the herb Thermopsis lupinoides were systematically investigated, which led to the isolation of 39 quinolizidine alkaloids (QAs) (1−39), including 14 new QAs (1−14) and 14 isoflavones (40−53). Their structures were elucidated through comprehensive spectroscopic data analysis (IR, UV, NMR, HRESIMS), ECD calculations, and Xray crystallography. The antitomato spotted wilt virus (TSWV) and antifungal (against Botrytis cinerea, Gibberella zeae, Phytophythora capsica, and Alternaria alternata) and insecticidal (against Aphis fabae and Tetranychus urticae) activities of the isolated compounds were screened using the lesion counting method, mycelial inhibition assay, and spray method, respectively. The bioassay results showed that 34 exhibited excellent protective activity against TSWV, with an EC 50 value of 36.04 μg/mL, which was better than that of the positive control, ningnanmycin (86.03 μg/mL). The preliminary mechanistic exploration illustrated that 34 induced systemic acquired resistance in the host plant by acting on the salicylic acid signaling pathway. Moreover, 1 showed significant antifungal activity against B. cinerea (EC 50 value of 20.83 μg/mL), while 2 exhibited good insecticidal activity against A. fabae (LC 50 value of 24.97 μg/mL). This research is promising for the invention of novel pesticides from QAs with high efficiency and satisfactory ecological compatibility.

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Section: Journal Of Agricultural Andsupporting

confidence: 55%

Quinolizidine Alkaloids and Isoflavones from the Herb of Thermopsis lupinoides and Their Antiviral, Antifungal, and Insecticidal Activities

Zhang,

Tian,

Zhang

et al. 2024

J. Agric. Food Chem.

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“…Indeed, chiral bicyclic phosphines often represent the ideal balance between nucleophilicity and facility of performing the P III /P V redox cycling, while having a congested chiral structure that can achieve good stereoselectivity [8b] . The direct formation of N ‐aryl‐pyrroles 4 a – c can be explained by the direct addition of the nitrogen atom of 1 to DAAD substrate 2 , following a cyclization/dehydration process, without the use of phosphine [17a–c,18] . Indeed, with more nucleophilic substrate 1 c and using “Condition B” without phosphine, pyrrole 4 c was isolated.…”

Section: Methodsmentioning

confidence: 99%

Phosphine‐Catalyzed Synthesis of Chiral N‐Heterocycles through (Asymmetric) P(III)/P(V) Redox Cycling

2021

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Phosphine-catalyzed tandem Michael addition/intramolecular Wittig reactions have been developed for the synthesis of chiral 2,5-dihydro-1H-pyrrole and tetrahydropyridine derivatives. These processes have been rendered catalytic in phosphine, thanks to the in situ reduction of phosphine oxide by phenylsilane. Furthermore, catalytic and asymmetric P(III)/P(V) processes were implemented using enantiopure chiral phosphines.

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“…[4] Pyrrole derivatives are present in the structure of many natural products such as vitamin B12, chlorophyll heme, bile pigments, and marine source-derived pyrrole alkaloids. [5] Vitamin B12 and chlorophyll heme contain four pyrrole rings in their structures. Also, pyrrole derivatives exist in the structure of the most drugs.…”

Section: Introductionmentioning

confidence: 99%

“…Lamellarin O, Q, R have anticancer activity. [5] Atorvastatin, an inhibitor of HMG-CoA reductase, acts as a cholesterol-lowering agent, [18] and Pyrrolnitrin is an antifungal agent. [19] According to the important properties of pyrroles, synthesis of these compounds has been very much considered.…”

Section: Introductionmentioning

confidence: 99%

Review on synthesis of pyrrole derivatives promoted by nanoparticles

Rostami

Shiri

2021

Applied Organom Chemis

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Pyrrole derivatives are a special class of heterocycle compounds that have many biological and pharmacological activities. Also, these compounds are one important portion of natural products which give particular properties to these compounds. In recent years, use of different nanoparticles for the organic synthesis is increased. In this review, we focused on the application of different nanoparticles in the synthesis of pyrrole derivatives.

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Metal-free synthesis of polysubstituted pyrroles using surfactants in aqueous medium

Cited by 18 publications

References 53 publications

Quinolizidine Alkaloids and Isoflavones from the Herb of Thermopsis lupinoides and Their Antiviral, Antifungal, and Insecticidal Activities

Quinolizidine Alkaloids and Isoflavones from the Herb of Thermopsis lupinoides and Their Antiviral, Antifungal, and Insecticidal Activities

Phosphine‐Catalyzed Synthesis of Chiral N‐Heterocycles through (Asymmetric) P(III)/P(V) Redox Cycling

Review on synthesis of pyrrole derivatives promoted by nanoparticles

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