Synthesis of 7‐amino‐1,4‐dihydro‐4‐oxo‐6‐(trifluoromethyl)‐1,8‐naphthyridines. The use of methylidenemalonate as an activating group and a sulfur assisted cyclization | Zendy

Bridges A. J. | Zendy; Sanchez J. P. | Zendy

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Synthesis of 7‐amino‐1,4‐dihydro‐4‐oxo‐6‐(trifluoromethyl)‐1,8‐naphthyridines. The use of methylidenemalonate as an activating group and a sulfur assisted cyclization

Author(s) -

Bridges A. J.,

Sanchez J. P.

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.5570270602

Subject(s) - chemistry , trifluoromethyl , pyridine , annulation , electrophile , nucleophile , reagent , ring (chemistry) , sulfur , group (periodic table) , medicinal chemistry , ion , combinatorial chemistry , organic chemistry , catalysis , alkyl

2,6‐Dichloro‐3‐(trifluoromethyl)pyridine 3 was used to develop a six‐step preparation of 7‐amino‐4‐oxo‐6‐(trifluoromethyl)naphthyridines. The CF 3 group deactivated the pyridine ring towards both nucleophiles and electrophiles. A new reagent for pyridone annulation, the aminomethylidenemalonate anion, is described, along with several strategies to manipulate the electron density of substituted pyridines.

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