Premium
2,1‐benzisothiazoles. XIII . Intermediates and products in the sulfur extrusion reaction of 2,1‐benzisothiazolin‐3(1 H )‐one. A new synthesis of 11 H ‐pyrido[2,1‐ b ]quinazolin‐11‐one (“pyracridone”)
Author(s) -
Davis Michael,
Hook Robert J.,
Wu Wen Yang
Publication year - 1984
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.5570210219
Subject(s) - chemistry , sulfur , ketene , nucleophile , imine , pyridine , derivative (finance) , medicinal chemistry , organic chemistry , catalysis , financial economics , economics
Abstract Triethyl phosphite abstracts sulfur from 2,1‐benzisothiazolin‐3(1 H )‐one (1); a reaction intermediate is the spirocyclic compound 11 , and products include the benzoxazine 6 and polyanthraniloyl compounds. In the presence of pyridine, pyracridone ( 13 ) is formed. The ketene‐imine 9 is probably not an intermediate in these reactions. The reactions of other nucleophiles with 1 and with its N ‐methyl derivative 15 , have been examined.