A new ring transformation of 3‐halo‐2‐azidopyridine 1‐oxides. A novel synthesis of 1,2‐oxazin‐6‐ones | Zendy

Abramovitch Rudolph A. | Zendy; Shinkai Ichiro | Zendy; Cue Berkeley W. | Zendy; Ragan Francis A. | Zendy; Atwood Jerry L. | Zendy

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A new ring transformation of 3‐halo‐2‐azidopyridine 1‐oxides. A novel synthesis of 1,2‐oxazin‐6‐ones

Author(s) -

Abramovitch Rudolph A.,

Shinkai Ichiro,

Cue Berkeley W.,

Ragan Francis A.,

Atwood Jerry L.

Publication year - 1976

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.5570130247

Subject(s) - chemistry , ring (chemistry) , halo , substituent , hydrolysis , stereochemistry , crystallography , organic chemistry , physics , quantum mechanics , galaxy

The course of the thermal ring‐opening and recyclization of 2‐azidopyridine 1‐oxides is radically altered by the presence of a 3‐halo substituent. Provided the 6‐position is blocked, recyclization leads to a 6‐cyano‐6‐halo‐1,2‐oxazine which hydrolyzes very readily to the 6 H ‐1,2‐oxazin‐6‐one. The structure of 4‐bromo‐3‐methyl‐6 H ‐1,2‐oxazin‐6‐one so obtained was confirmed by single crystal X‐ray analysis. If the 6‐position is not blocked, the product undergoes a further ring opening to give ( Z )‐β‐cyanoacrylates.

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