Nitration studies of naphtho[2,3‐ c ][1,2,5]thiadiazole | Zendy

Smith Walter T. | Zendy; Patterson John M. | Zendy; Kovelesky Albert C. | Zendy

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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.

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