Haloacetylated enol ethers.  5  [5]. Heterocyclic ring closure reactions of β‐alkoxyvinyl dichloromethyl ketones with hydroxylamine | Zendy

Martins Marcos A. P. | Zendy; Zoch Ala. | Zendy; Flores Alex F. C. | Zendy; Clar Günter | Zendy; Zanatta Nilo | Zendy; Bonacorso Helio G. | Zendy

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Haloacetylated enol ethers. 5 [5]. Heterocyclic ring closure reactions of β‐alkoxyvinyl dichloromethyl ketones with hydroxylamine

Author(s) -

Martins Marcos A. P.,

Zoch Ala.,

Flores Alex F. C.,

Clar Günter,

Zanatta Nilo,

Bonacorso Helio G.

Publication year - 1995

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570320307

Subject(s) - chemistry , enol , hydroxylamine , bicyclic molecule , sulfuric acid , ring (chemistry) , yield (engineering) , medicinal chemistry , pyridine , ketone , organic chemistry , hydroxylamine hydrochloride , oxime , catalysis , materials science , metallurgy

The β‐alkoxyvinyl dichloromethyl ketones 1a‐d are cyclocondensed with hydroxylamine hydrochloride in pyridine to afford the 5‐hydroxy‐5‐dichloromethyl‐4,5‐dihydroisoxazoles 2a‐d in good yield. The cyclo‐condensation of compound 1c gave, together with 2c , 3‐cyano‐2‐hydroxy‐2‐dichloromethyltetrahydrofuran 5c. The dehydratation of compounds 2a,b , derived from acyclic enol ethers, with concentrated sulfuric acid at 30°, led the corresponding 5‐dichloromethylisoxazoles 3a,b. The dehydratation of compounds 2c,d , derived from cyclic enol ethers, with concentrated sulfuric acid at 30°, led the bicyclic 4,5‐dihydroisoxazoles 4c,d , and at 55°, a competitive rearrangement reaction gives the 3‐cyano‐2‐hydroxy‐2‐dichloromethyl‐2 H ‐pyran 5d.

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