Pincer ligands based on α-amino acids: I. Synthesis of polydentate ligands from pyrrole-2,5-dicarbaldehyde

Knizhnikov, V. A.; Borisova, Nataliya E.; Yurashevich, N. Ya.; Popova, L. A.; Chernyad’ev, A. Yu.; Зубрейчук, З. П.; Reshetova, M. D.

doi:10.1134/s1070428007060097

Cited by 20 publications

(16 citation statements)

References 10 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…According to a known procedure, 19 a solution of compound 30 (0.52 g, 1.2 mmol) in CH 2 Cl 2 (50 mL) was carefully treated with TiCl 4 at -78 °C for 40 h. Then the reaction was quenched with aqueous saturated NaHCO 3 solution and extracted with EtOAc (4 × 30 mL). The combined organic extracts were washed with brine, dried over MgSO 4 , filtrated and evaporated.…”

Section: Xylapyrroside B (2) and Acortatarin A (4) (Methods 2)mentioning

confidence: 99%

See 1 more Smart Citation

Xylapyrrosides A and B, two rare sugar-morpholine spiroketal pyrrole-derived alkaloids from Xylaria nigripes: isolation, complete structure elucidation, and total syntheses

Xiong

Huang

et al. 2015

Tetrahedron

View full text Add to dashboard Cite

Section: Xylapyrroside B (2) and Acortatarin A (4) (Methods 2)mentioning

confidence: 99%

“…This precursor was envisioned to be available from a protected 2-formyl-5-hydroxymethyl-pyrrole (7) by N-alkylation with the epoxide 6, 8,19 which in turn could be generated from the commercially available aldehyde 8. Scheme 1.…”

Section: Total Synthesismentioning

confidence: 99%

Xylapyrrosides A and B, two rare sugar-morpholine spiroketal pyrrole-derived alkaloids from Xylaria nigripes: isolation, complete structure elucidation, and total syntheses

Xiong

Huang

et al. 2015

Tetrahedron

View full text Add to dashboard Cite

“…With bromides 10a and 10b in hand to advance the synthesis, we decided to test the outcome of S N 2 coupling with bisformyl pyrrole 11 . The three-step sequence [ 18 ] with assistance of microwave for the Vilsmeier–Haack formylation [ 19 ] proceeded well to afford 11 in 45 % yield (Scheme 4 ). To our delight, 12a (nearly 1/1 diastereoisomers) was generated directly in about 40 % yield using NaH [ 10 ] with unanticipated formation of semiacetal ring which was confirmed by 1D and 2D NMR.…”

Section: Resultsmentioning

confidence: 99%

Cascade N-Alkylation/Hemiacetalization for Facile Construction of the Spiroketal Skeleton of Acortatarin Alkaloids with Therapeutic Potentiality in Diabetic Nephropathy

Cao

Sun

et al. 2014

Nat. Prod. Bioprospect.

View full text Add to dashboard Cite

Graphical AbstractThe Acortatarin alkaloids exhibit a promising perspective against diabetic nephropathy and other ROS-linked diseases. Facile construction of the dioxaspirocycle motif was realized through tandem N-alkylation/hemiacetalization between pyrrole units and the corresponding halo alcohols, which were derived in turn from convenient halomethylation of chiral lactones in natural carbohydrates pool.Electronic supplementary materialThe online version of this article (doi:10.1007/s13659-014-0049-8) contains supplementary material, which is available to authorized users.

show abstract

“…1H-Pyrrole-2,5-dicarbaldehyde [34] and 2,3-bis-hydroxylamino-2,3-dimethylbutane [35] were synthesized by known methods. Commercially available reagents and solvents were used without further purification.…”

Section: Reagents and General Methodsmentioning

confidence: 99%

(Pyrrole-2,5-Diyl)-Bis(Nitronyl Nitroxide) and-Bis(Iminonitroxide): Specific Features of the Synthesis, Structure, and Magnetic Properties

et al. 2020

View full text Add to dashboard Cite

In contrast to diradicals connected by alternant hydrocarbons, only a few studies have addressed diradicals connected by nonalternant hydrocarbons and their heteroatom derivatives. Here, the synthesis, structure, and magnetic properties of pyrrole-2,5-diyl–linked bis(nitronyl nitroxide) and bis(iminonitroxide) diradicals are described. The diradicals show characteristic electron spin resonance spectra in dilute glassy solutions, from which conclusions about the presence of distinct conformations, their symmetry, and interspin distance were made. X-ray diffraction analysis of the diradicals revealed that paramagnetic moieties lie in the plane of the pyrrole ring, because of the formation of an intramolecular hydrogen bond, ONO…H−N, with O…H distances of 2.15–2.23 Å. The N–O groups participating in the formation of H-bonds have greater bond lengths (~1.29 Å) as compared with nonparticipating groups (~1.27 Å). The nitronyl nitroxide and iminonitroxide diradicals showed an intramolecular antiferromagnetic interaction, with J = −77.3 and −22.2 cm−1, respectively (H = −2JS1⋅S2).

show abstract

Pincer ligands based on α-amino acids: I. Synthesis of polydentate ligands from pyrrole-2,5-dicarbaldehyde

Cited by 20 publications

References 10 publications

Xylapyrrosides A and B, two rare sugar-morpholine spiroketal pyrrole-derived alkaloids from Xylaria nigripes: isolation, complete structure elucidation, and total syntheses

Xylapyrrosides A and B, two rare sugar-morpholine spiroketal pyrrole-derived alkaloids from Xylaria nigripes: isolation, complete structure elucidation, and total syntheses

Cascade N-Alkylation/Hemiacetalization for Facile Construction of the Spiroketal Skeleton of Acortatarin Alkaloids with Therapeutic Potentiality in Diabetic Nephropathy

(Pyrrole-2,5-Diyl)-Bis(Nitronyl Nitroxide) and-Bis(Iminonitroxide): Specific Features of the Synthesis, Structure, and Magnetic Properties

Contact Info

Product

Resources

About