Synthesis of N,N‐Disubstituted Lactone Hydrazones via (Sulfonylimino)‐ethers

Fritschi, Stephan P.; Vasella, Andrea

doi:10.1002/hlca.19910740837

Cited by 26 publications

(14 citation statements)

References 22 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…However, it was consistent with the observed diacetylation of 4-amino groups in related 1,2,4-triazoles reported by other research groups. [70,71] To obtain pure tetraacetate 20 in good yield it was crucial to reflux the reaction mixture vigorously and to immerse the reaction vessel in a preheated oil bath (160 8C) rather than increasing the temperature gradually. Inseparable mixtures of differently acetylated compounds were obtained when these directions were not followed.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Some First‐Row Transition‐Metal Complexes of the 1,2,4‐Triazole‐Based Bis(terdentate) Ligands TsPMAT and PMAT

Klingele

Moubaraki

Murray

et al. 2005

Chemistry A European J

View full text Add to dashboard Cite

The employment of a strategy based on nucleophilic substitution, rather than Schiff base condensation, for the preparation of 1,2,4-triazole-based ligands has been investigated and has led to the synthesis of two new ligands, 4-amino-3,5-bis{[N-(2-pyridylmethyl)-N-(4-toluenesulfonyl)amino]methyl}-4H-1,2,4-triazole (TsPMAT, 14) and 4-amino-3,5-bis{[(2-pyridylmethyl)amino]methyl}-4H-1,2,4-triazole (PMAT, 15). These are the first examples of bis(terdentate) ligands incorporating the 1,2,4-triazole unit. TsPMAT (14) forms a dinuclear 2:2 complex with Co(BF4)2.6 H2O even when reacted in a metal-to-ligand molar ratio of 2:1. Similarly, the reaction of PMAT (15) with Mn(ClO4)2.6H2O or M(BF4)2.6 H2O (M=Fe, Co, Ni, Zn) in a ligand-to-metal molar ratio of 1:1 has afforded a series of complexes with the general formula [M(II) (2)(PMAT)2]X4. The metal centres in these complexes of TsPMAT (14) and PMAT (15) are encapsulated by two ligand molecules and doubly bridged by the N2 units of the 1,2,4-triazole moieties, which gives rise to N6 coordination spheres that are strongly distorted from octahedral, as evidenced by the X-ray crystal structure analyses of [Co(II) (2)(TsPMAT)(2)](BF(4))(4)6 MeCN (246 MeCN) and [Fe(II) 2(PMAT)2](BF4)4DMF (27DMF). Studies of the magnetic properties of [Co(II) 2(TsPMAT)2](BF4)4.4 H2O (244 H2O), [Mn(II) 2(PMAT)2](ClO4)4 (26), and [Co(II) 2(PMAT)2](BF4)4 (28) have revealed weak antiferromagnetic coupling (J=-3.3, -0.16, and -2.4 cm(-1), respectively) between the two metal centres in these complexes.

show abstract

Section: Resultsmentioning

confidence: 99%

Synthesis and Some First‐Row Transition‐Metal Complexes of the 1,2,4‐Triazole‐Based Bis(terdentate) Ligands TsPMAT and PMAT

Klingele

Moubaraki

Murray

et al. 2005

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…Preparation of Trifluoromethylsulfonyl Azide Solution: According to Fritschi and Vasella [28]. Synthesis of a-Nitro-a-diazo Esters 17.…”

Section: Experimental Partmentioning

confidence: 99%

“…We previously reported [27] a novel diazo-transfer reaction involving the treatment of a MeCN/hexanes solution of (trifluoromethyl)sulfonyl (trityl) azide [28] and an a-nitro ester or ketone with pyridine, which affords the corresponding a-nitro-…”

mentioning

confidence: 99%

Synthesis of α‐Nitro‐α‐diazocarbonyl Derivatives and Their Applications in the Cyclopropanation of Alkenes and in OH Insertion Reactions

Charette¹,

Wurz²,

Ollevier³

2002

Helvetica Chimica Acta

View full text Add to dashboard Cite

Dedicated to Professor Dieter Seebach on the occasion of his 65th birthday A facile and highly efficient method for the preparation of a-nitro-a-diazocarbonyl derivatives by a diazotransfer reaction involving (trifluoromethyl)sulfonyl azide has been developed. These substrates undergo a rhodium-catalyzed cyclopropanation reaction with a variety of alkenes. A systematic study of the reaction indicated that the diastereoselectivity of the cyclopropanation could be effectively controlled through the modification of the steric bulk of the diazo reagent. A novel OÀH insertion reaction of the metalÀcarbene complex derived from the a-nitro-a-diazocarbonyl reagent afforded the corresponding novel a-nitro-a-alkoxy carbonyl derivatives.

show abstract

“…The recently performed X‐ray analysis showed that it has a lamellar crystal structure with the distance between the layers of 3.4 Å . The X‐ray structure for complexes of triflamide with tetrahydro‐ N ‐(4 H ‐1,2,4‐triazol‐4‐yl)‐2 H ‐pyran‐2‐imine and 2,4,8,10‐tetraoxospiro[5.5]undecane was also determined …”

Section: Introductionmentioning

confidence: 99%

Acid‐base properties and supramolecular structure of N‐[(hydroxymethyl)triazolyl]triflamides: DFT, ab initio, and FTIR study

Shainyan

Chípanina

Oznobikhina

et al. 2016

J of Physical Organic Chem

View full text Add to dashboard Cite

For N‐{[2‐(hydroxymethyl)‐2H‐1,2,3‐triazolyl‐4‐yl]methyl}triflamide 1, N‐{[2‐(hydroxymethyl)‐2H‐1,2,3‐triazolyl‐4‐yl]methyl}‐N‐phenyltriflamide 2, and N,N‐bis{[2‐(hydroxymethyl)‐2H‐1,2,3‐triazolyl‐4‐yl]methyl}triflamide 3, the proton affinities of the triazole nitrogen atoms and the hydroxy and sulfonyl oxygen atoms as well as the energies of formation of the conformers with intramolecular H‐bonds and dimers with intermolecular NH⋯N, OH⋯N, OH⋯O═S, and NH⋯O═S H‐bonds were calculated by density functional theory and second‐order Møller‐Plesset perturbation methods. Quantum Theory of Atoms in Molecules analysis was performed to investigate the nature of H‐bonds. According to Fourier transform infrared spectroscopy, in CH2Cl2 solution, the monomeric molecules of 1 to 3 exist in the equilibrium with cyclic dimers having the OH⋯N hydrogen bonds.

show abstract

Synthesis of N,N‐Disubstituted Lactone Hydrazones via (Sulfonylimino)‐ethers

Cited by 26 publications

References 22 publications

Synthesis and Some First‐Row Transition‐Metal Complexes of the 1,2,4‐Triazole‐Based Bis(terdentate) Ligands TsPMAT and PMAT

Synthesis and Some First‐Row Transition‐Metal Complexes of the 1,2,4‐Triazole‐Based Bis(terdentate) Ligands TsPMAT and PMAT

Synthesis of α‐Nitro‐α‐diazocarbonyl Derivatives and Their Applications in the Cyclopropanation of Alkenes and in OH Insertion Reactions

Acid‐base properties and supramolecular structure of N‐[(hydroxymethyl)triazolyl]triflamides: DFT, ab initio, and FTIR study

Contact Info

Product

Resources

About