The Chemistry of the Oxazoles.

Wiley, Richard H.

doi:10.1021/cr60118a002

Cited by 61 publications

(19 citation statements)

References 71 publications

(250 reference statements)

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“…The crystal structure analysis reported here shows that a reaction between the cyanide ion and the ethanolamine cation has occurred (Scheme 2) to cause ring closure and the formation of an N-methylated 1,3-oxazole ring with a 2-iminium group, which acts as cation guest in a 3D anionic copper(I) cyanide network. Oxazole chemistry is a mature field [2][3][4][5] and oxazoles play an important role in pharmaceutical chemistry [6]. Oxazole synthesis has been achieved in at least fifteen different types of reactions [4], but we are not aware of a reaction similar to that reported here.…”

Section: Introductionmentioning

confidence: 82%

Poly[3-methyl-1,3-oxazolidin-2-iminium[µ3-cyanido-tri-µ2-cyanido-κ9C:N-tricuprate(I)]]

Rachid

Corfield

2021

Molbank

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The unexpected formation of an oxazole ring has occurred during synthesis of a copper(I) cyanide network polymer as part of our ongoing studies of the structural chemistry of these networks. Crystals of the title compound were formed during the synthesis of a previously reported CuCN network solid containing protonated N-methylethanolamine and have been characterized by single crystal X-ray structure analysis. The structure shows well-defined oxazole-2-iminium cations sitting in continuous channels along the short a-axis of the crystal in a new three-dimensional copper(I) cyanide polymeric network. Evidently, a reaction has occurred between the cyanide ion and the protonated N-methylethanolamine base.

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Section: Introductionmentioning

confidence: 82%

Poly[3-methyl-1,3-oxazolidin-2-iminium[µ3-cyanido-tri-µ2-cyanido-κ9C:N-tricuprate(I)]]

Rachid

Corfield

2021

Molbank

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“…This reaction involves the acidified condensation of equimolar amounts of cyanohydrins and aromatic aldehyde in dry ether. 3 This synthesis was discovered by Hermann Emil Fischer in 1896, who found that 2,5-diphenyloxazole hydrochloride precipitated when HCl was passed through an absolute ether solution of benzaldehyde and benzaldehyde cyanohydrins. 3 This synthetic route is typically high yielding (~80%).…”

Section: Synthesis Of Oxazolines and Oxazolesmentioning

confidence: 99%

Towards the synthesis of photobactin: methodology and metal binding aspects

Shuoprasad¹

2021

Preprint

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Siderophores are metal-typically iron-chelating compounds that have received countless attention in research, as they can play a role in medicine intended for drug delivery and iron overload treatment. The synthesis of Photobactin has been of interest as it has been previously isolated (<10 mg) from Photorhabdus luminescence and has not once been synthesized. This thesis examined the preparation of Photobactin using a multi-step approach: synthesizing two building blocks individually and coupling them together with an amide coupling reagent. Both building blocks were synthesized successfully. However, the deprotection of the ester group on one of the building blocks has been uncooperative, and therefore the total synthesis of Photobactin was not achieved. Moreover, DFT computation calculations were performed to study Photobactin binding properties with Fe3+. According to the results, iron (Fe3+) is likely to form a hexadentate (6-coordinate ligand) or a tetradentate (4-coordinate ligand) complex with Photobactin. Each of the compounds leading to Photobactin was characterized using 1H and 13C-NMR. Some compounds were characterized using elemental analysis and performing 2D-NMR (COSY, HMBC, and HSQC) to make final assignments.

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“…Owing to the highly fluorescent behaviour emanating from their structure, aryl-substituted oxazoles are an interesting class of compounds (Wiley, 1945). Derived from this property, some 2,5-diaryloxazoles have found commercial application as solutes in liquid scintillators (Bell & Hayes, 1958).…”

Section: Commentmentioning

confidence: 99%

Them-phenylene-bridged bis-oxazole 4,4′,5,5′-tetraphenyl-2,2′-m-phenylenedi-1,3-oxazole and its bulkily substituted analogue 4,4′,5,5′-tetrakis(4-tert-butylphenyl)-2,2′-m-phenylenedi-1,3-oxazole

Hübscher¹,

Felsmann²,

Seichter³

et al. 2010

Acta Crystallogr C

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The title m-phenylene-bridged bis-oxazoles, C(36)H(24)N(2)O(2), (I), and C(52)H(56)N(2)O(2), (II), feature different aryl substituents in the 4- and 5-positions of the oxazole units. In the solid state, aside from the different twist of the peripheral aryl rings, the molecules show distinctly different conformations, with anti and syn orientations of the O and N atoms for (I) and (II), respectively. Connected with this property, in the crystal structure of (I), extensive π-stacking is found between the molecules, while the crystal structure of (II) only involves dimer formation as the prominent packing motif.

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The Chemistry of the Oxazoles.

Cited by 61 publications

References 71 publications

Poly[3-methyl-1,3-oxazolidin-2-iminium[µ3-cyanido-tri-µ2-cyanido-κ9C:N-tricuprate(I)]]

Poly[3-methyl-1,3-oxazolidin-2-iminium[µ3-cyanido-tri-µ2-cyanido-κ9C:N-tricuprate(I)]]

Towards the synthesis of photobactin: methodology and metal binding aspects

Them-phenylene-bridged bis-oxazole 4,4′,5,5′-tetraphenyl-2,2′-m-phenylenedi-1,3-oxazole and its bulkily substituted analogue 4,4′,5,5′-tetrakis(4-tert-butylphenyl)-2,2′-m-phenylenedi-1,3-oxazole

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