The synthesis of heteroaromatic nitro compounds from 3‐nitrochromone | Zendy

Haas Georges | Zendy; Stanton James L. | Zendy; Winkler Tammo | Zendy

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The synthesis of heteroaromatic nitro compounds from 3‐nitrochromone

Author(s) -

Haas Georges,

Stanton James L.,

Winkler Tammo

Publication year - 1981

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.5570180336

Subject(s) - chemistry , nitro , yield (engineering) , intramolecular force , nucleophile , medicinal chemistry , condensation , catalysis , organic chemistry , alkyl , materials science , physics , metallurgy , thermodynamics

3‐Nitrochromone ( 1 ) reacts with a series of nucleophiles by Michael addition followed by intramolecular condensation to yield pyrrolyl ( 2 ), phenyl ( 3 ), pyridyl ( 4 ), pyrido ( 5,6 ), pyrimidyl ( 7 ) and pyrazolyl ( 8 ) nitro derivatives. The reactions proceed under basic catalysis in 39–78% yields. Conversion of 4 to 3,4‐dihydrobenzofuro[3,2‐ b ]quinol‐1‐(2H)one ( 12 ) is also described. Carbon‐13 data for 2, 5, 6 and 8 are discussed. The one bond C,H coupling constants in the nitropyridines are also reported and used as an analytical tool.

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