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Preparation of benzofuroxans and benzofurazans of 2,3,4,5‐tetrahydrobenzo[b] [1,4]dioxocin and related compounds
Author(s) -
Takakis Ioannis M.,
Hadjimihalakis Phaedon M.
Publication year - 1990
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.5570270212
Subject(s) - nitration , chemistry , yield (engineering) , derivative (finance) , medicinal chemistry , organic chemistry , stereochemistry , materials science , economics , financial economics , metallurgy
The novel benzofuroxans 1d, 2 and benzofurazans 3,4 have been prepared in good yields. Nitration of 5c furnished the mononitro‐derivatives 6a and 6b in the unusually high relative ratio 6a:6b of 23:77. Direct nitration of 5c or 6a + 6b afforded the unexpected dinitro‐derivative 8b as the major product along with the isomeric 8a, 8c and 8d . Improvement in the yield of 5c (to 86%) is reported.
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