Kobalt‐katalysiert Cycloadditionen von Alkinen und Nitrilen zu Pyridinen: Ein neuer Zugang zu Pyridoxin (Vitamin B 6 ) | Zendy

Geiger Rudolf E. | Zendy; Lalonde Michel | Zendy; Stoller Hansijörg | Zendy; Schleich Kuno | Zendy

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Kobalt‐katalysiert Cycloadditionen von Alkinen und Nitrilen zu Pyridinen: Ein neuer Zugang zu Pyridoxin (Vitamin B 6 )

Author(s) -

Geiger Rudolf E.,

Lalonde Michel,

Stoller Hansijörg,

Schleich Kuno

Publication year - 1984

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19840670513

Subject(s) - chemistry , pyridoxine hydrochloride , cycloaddition , pyridoxine , medicinal chemistry , curtius rearrangement , pyridine , hydrolysis , catalysis , stereochemistry , organic chemistry , biochemistry

Cobalt‐Catalyzed Cycloaddition of Alkynes and Nitriles to Pyridines: A New Route to Pyridoxine (Vitamin B 6 ) A new synthesis of pyridoxine hydrochloride ( 1 ) based on a Co‐catalyzed cycloaddition of MeCN with substituted di(2‐propynyl) ethers ( 3 and 16 ) is described. The reaction sequences following cycloaddition and leading to 1 involve as key steps the rearrangement f the pyridine‐ N ‐oxide 6 to the 3‐hydroxypyridine 7 with Ac 2 O and a modified Curtius rearrangement of the acid 19 and subsequent diazotation and hydrolysis to the same pyridoxine precursor 7 , respectively. The intermediate 7 is transformed to 1 by well‐known procedures.

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