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Nitration studies of naphtho[2,3‐ c ][1,2,5]thiadiazole
Author(s) -
Smith Walter T.,
Patterson John M.,
Kovelesky Albert C.
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.5570270313
Subject(s) - nitration , chemistry , anthracene , yield (engineering) , medicinal chemistry , naphthalene , hydrogen chloride , recrystallization (geology) , derivative (finance) , chloride , organic chemistry , paleontology , materials science , economics , financial economics , metallurgy , biology
Nitration of naphtho[2,3‐ c ][1,2,5]thiadiazole gives the 5‐nitro derivative in 61–66% yield. Chlorination of this product apparently gives an unstable addition product which loses hydrogen chloride on recrystallization to give 4‐chloro‐8‐nitronaphtho[2,3‐ c ][1,2,5]thiadiazole. Thus, naphtho[2,3‐ c ][1,2,5]thiadiazole under nitrating conditions behaves as a 2‐substituted naphthalene rather than as an anthracene analog.