Introduction of Water-Solubilizing Groups at the Lower Rim of Tolylpyridine-Bridged Cavitands

Pirondini, Laura; Melegari, Monica; Pinalli, Roberta; Dalcanale, Enrico

doi:10.1080/10610270600932826

Cited by 3 publications

(3 citation statements)

References 16 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…808 The monosubstituted derivative 264 was obtained in 41% yield using a 3.3:1.8:2.4:1 molar ratio of phthalimide, DEAD, Ph 3 P, and R-cyclodextrin with DMF as a solvent at room temperature. A mixture of three bis-isomers of 265 (A, B, C) and the mono compound (yields of 22%, 9.5%, 4.6%, and 13%, respectively) were obtained 809 In a reaction reported by Morita and Krause, the allenyl alcohol 266 was converted to the R-aminoallene 267 in good yield with complete inversion as depicted in Scheme 65. 810,811 N-Alkylation of nitrophthalimide using DEAD incorporated nanoporous magnesium aluminometasilicate tablets has been reported recently.…”

Section: N-alkylation Using Phthalimide and Related Imidesmentioning

confidence: 98%

“…All these intermediates could be successfully converted to the amino compounds by hydrazinolysis. Another recent report, by Pirondini et al, involved phthalimide mediated conversion of −OH to NH 2 (and then to hydrochloride) at the lower rim of tolylpyridine-bridged cavitands for use as water-soluble molecular receptors . In a reaction reported by Morita and Krause, the allenyl alcohol 266 was converted to the α-aminoallene 267 in good yield with complete inversion as depicted in Scheme . , N -Alkylation of nitrophthalimide using DEAD incorporated nanoporous magnesium aluminometasilicate tablets has been reported recently.…”

Section: Amines Amides (Including Nucleobases) or Azides As Nucleophilesmentioning

confidence: 99%

See 1 more Smart Citation

Mitsunobu and Related Reactions: Advances and Applications

et al. 2009

View full text Add to dashboard Cite

His research interests include Organophosphorus Chemistry and Main Group Chemistry. He has over 115 publications so far and is a fellow of the Indian Academy of Sciences, Bangalore. N. N. Bhuvan Kumar was born in Cherukupalli, Guntur, India. After completing his B.Sc. from Nagarjuna University, he joined the School of Chemistry, University of Hyderabad, as a postgraduate student in the year 2000 and obtained his Master's degree in Chemistry. Currently, he is pursuing a Ph.D. on Organophosphonates under the supervision of Prof. K. C. Kumara Swamy. E. Balaraman was born in Kancheepuram, Chennai, India, in 1980. He received his M.Sc. in Chemistry from Vivekananda College [Madras University (2002)] and his Ph.D. degree in the areas of organophosphonates and modified BINOLs under the guidance of Prof. K. C. Kumara Swamy. Presently he is a postdoctoral fellow with Professors David Milstein and Ronny Neumann at the Weizmann Institute of Science, Israel. K. V. P. Pavan Kumar was born in Hyderabad (Andhra Pradesh), India, in 1979. He obtained his B.Sc. (Chemistry Honors) and M.Sc. (Chemistry) degrees from Sri Sathya Sai Institute of Higher Learning, Puttaparthi, A.P., India. He obtained his Ph.D. degree under the guidance of Prof. K. C. Kumara Swamy in October 2006. Presently he is working as a postdoctoral fellow in the area of hydroamination reactions using new titanium catalysts with Prof. Pierre Le Gendre at the Universite ´de Bourgogne, France.

show abstract

Section: N-alkylation Using Phthalimide and Related Imidesmentioning

confidence: 98%

Section: Amines Amides (Including Nucleobases) or Azides As Nucleophilesmentioning

confidence: 99%

Mitsunobu and Related Reactions: Advances and Applications

et al. 2009

View full text Add to dashboard Cite

show abstract

“…Water solubility is achieved through the covalent attachment of poly(ethylene glycol) (PEG) chains16,19 in both the legs and the top bridge of cavitands 3a , b . We chose PEG chains over charged water‐solubilizing groups such as ammonium,20 carboxylate,12 phosphate,21 or sulfate20 salts to limit potential interactions with the diverse guests studied in inclusion complexation. We describe how the PEG groups attached to the bridge change the planar chirality properties of the molecule, as reflected in the 1 H NMR spectra 22–24…”

Section: Introductionmentioning

confidence: 99%

Resorcin[4]arene‐Based Molecular Baskets and Water‐Soluble Container Molecules: Synthesis and ¹H NMR Host–Guest Complexation Studies

et al. 2014

View full text Add to dashboard Cite

Resorcin[4]arene‐based molecular baskets, with four free or methylene‐bridged HO groups, and water‐soluble container molecules bearing poly(ethylene glycol) chains of different lengths on the lower rim and cap have been synthesized. These cavitands, topped with p‐xylylene bridges, feature well‐defined cavities capable of encapsulating heteroalicyclic guests. Association constants (Ka) were determined by 1H NMR spectroscopy for the organic‐soluble molecular baskets in CDCl3 and for the water‐soluble container molecules in D2O/CD3CN (2:1). Opposite guest selectivities were observed in the two environments. Upon complexation, the water‐soluble hosts show changes in their 1H NMR spectra. In the absence of guests, the p‐xylylene bridge rotates rapidly on the 1H NMR timescale, revealing a time‐averaged achiral C2v structure, whereas this rotation is hindered by guest inclusion, resulting in spectra showing a racemic C2‐symmetric host, indicative of planar chirality.

show abstract

Preface to the Special ISMSC Issue of Supramolecular Chemistry

2007

Supramolecular Chemistry

View full text Add to dashboard Cite

Introduction of Water-Solubilizing Groups at the Lower Rim of Tolylpyridine-Bridged Cavitands

Cited by 3 publications

References 16 publications

Mitsunobu and Related Reactions: Advances and Applications

Mitsunobu and Related Reactions: Advances and Applications

Resorcin[4]arene‐Based Molecular Baskets and Water‐Soluble Container Molecules: Synthesis and ¹H NMR Host–Guest Complexation Studies

Preface to the Special ISMSC Issue of Supramolecular Chemistry

Contact Info

Product

Resources

About

Introduction of Water-Solubilizing Groups at the Lower Rim of Tolylpyridine-Bridged Cavitands

Cited by 3 publications

References 16 publications

Mitsunobu and Related Reactions: Advances and Applications

Mitsunobu and Related Reactions: Advances and Applications

Resorcin[4]arene‐Based Molecular Baskets and Water‐Soluble Container Molecules: Synthesis and 1H NMR Host–Guest Complexation Studies

Preface to the Special ISMSC Issue of Supramolecular Chemistry

Contact Info

Product

Resources

About

Resorcin[4]arene‐Based Molecular Baskets and Water‐Soluble Container Molecules: Synthesis and ¹H NMR Host–Guest Complexation Studies