Synthesis and nucleophilic displacement reactions of fluoropyrazine and 2‐fluoroquinoxaline | Zendy

Rutner Herman | Zendy; Spoerri Paul E. | Zendy

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Synthesis and nucleophilic displacement reactions of fluoropyrazine and 2‐fluoroquinoxaline

Author(s) -

Rutner Herman,

Spoerri Paul E.

Publication year - 1966

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.5570030408

Subject(s) - chemistry , sodium hydroxide , sodium cyanide , hydrolysis , nucleophile , halogen , sodium azide , hydrochloric acid , medicinal chemistry , sodium , pyrazine , sodium sulfite , nucleophilic aromatic substitution , hydroxide , nucleophilic substitution , organic chemistry , cyanide , catalysis , alkyl

An improved method for the preparation of fluoropyrazine (I) by halogen exchange and a synthesis of 2‐fluoroquinoxaline (II) by a Balz‐Schiemann reaction are presented. Compound I hydrolyzes slowly in 0.01 N sodium hydroxide, rapidly in 1.07 N sodium hydroxide at 26.00°. Compound II hydrolyzes 240 times faster than I in 0.01 N sodium hydroxide at 26.00°. Hydrolysis of I in 6 N hydrochloric acid at room temperature is slow. Compound I underwent nucleophilic reactions with formation of hydroxy, amino, methylamino, piperidino, benzylamino and anilinopyrazines. Pyrazinesulfonic acid was obtained from I and sodium sulfite and tetrazolo[1, 5‐ a ]pyrazine (IV), a novel ring system, from I and sodium azide.

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