The Synthetic Intermediate of Pyridoxine. I. A Novel Synthesis of 5-Alkoxy-2-carboxy-4-methyloxazole

Maeda, Itsutoshi; Takehara, Masahiro; Togo, Kazushi; Asai, Soichiro; Yoshida, Ryonosuke

doi:10.1246/bcsj.42.1435

Cited by 30 publications

(7 citation statements)

References 2 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Furthermore, oxalic ester derivatives of d,lalanine can be transformed to oxazole derivatives. [117] During recent years, several modifications of this approach hav been established by changing the reaction sequence and applying basic conditions. This has led to lower waste formation and an increased yield.…”

Section: Methodsmentioning

confidence: 99%

One Hundred Years of Vitamins—A Success Story of the Natural Sciences

Eggersdorfer¹,

Laudert²,

Létinois³

et al. 2012

Angew Chem Int Ed

255

209

View full text Add to dashboard Cite

The discovery of vitamins as essential factors in the diet was a scientific breakthrough that changed the world. Diseases such as scurvy, rickets, beriberi, and pellagra were recognized to be curable with an adequate diet. These diseases had been prevalent for thousands of years and had a dramatic impact on societies as well as on economic development. This Review highlights the key achievements in the development of industrial processes for the manufacture of eight of the 13 vitamins.

show abstract

Section: Methodsmentioning

confidence: 99%

One Hundred Years of Vitamins—A Success Story of the Natural Sciences

Eggersdorfer¹,

Laudert²,

Létinois³

et al. 2012

Angew Chem Int Ed

255

209

View full text Add to dashboard Cite

show abstract

“…In another study it was necessary to prepare oxazole-2carboxylates. 131 The reaction of a number of cyclodehydrating agents with methyl -methoxalylalanate 160 to give methyl 4-methyl-5-methoxyoxazole-2-carboxylate (161) under a variety of conditions was investigated. The reagent of choice for this cyclization was phosgene in triethylamine, affording 161 in 80% yield at room temperature for 10 min.…”

Section: Acylaziridine-oxazole Rearrangementsmentioning

confidence: 99%

Chemistry of oxazoles

Turchi¹,

Dewar²

1975

Chem. Rev.

328

114

View full text Add to dashboard Cite

“…First, this transformation looks like a widely used Robinson–Gabriel oxazole synthesis — cyclodehydration of N ‐acylaminoketones , where furan moiety can act as a source of carbonyl group. However, unlike the said method required such as acidic dehydrating agents as acetic anhydride, P 2 O 5 , PPA, triflic anhydride, this transformation proceeds under basic conditions.…”

Section: Resultsmentioning

confidence: 99%