Syntheses of 2-azafluorenones from 3-substituted 4-arylpyridines

Min Jen Shiao; Kang Hsiuan Liu; Pen Yuan Lin

doi:10.3987/COM-92-6199

Syntheses of 2-azafluorenones from 3-substituted 4-arylpyridines

Min Jen Shiao, Kang Hsiuan Liu, Pen Yuan Lin

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15 Citations (Scopus)

Abstract

3-Substituted 4-arylpyridines (5a-i) were synthesized in good yields by reaction of mixed copper, zinc aryl organometallics (2a-e) with 1-ethoxycarbonyl-pyridinium chlorides (1a-d) followed by o-chloranil oxidation under reflux in toluene. The 4-arylpyridines (5a-i) are obtained predominantly. Having compounds (5a-i) in hand, a convenient method was developed for the synthesis of 2-azafluorenones (7a-f) by using cyclization of 4-arylpyridines (5a-i) with polyphosphoric acid.

Original language	English
Pages (from-to)	507-518
Number of pages	12
Journal	Heterocycles
Volume	36
Issue number	3
DOIs	https://doi.org/10.3987/COM-92-6199
Publication status	Published - Mar 1 1993
Externally published	Yes

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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abstract = "3-Substituted 4-arylpyridines (5a-i) were synthesized in good yields by reaction of mixed copper, zinc aryl organometallics (2a-e) with 1-ethoxycarbonyl-pyridinium chlorides (1a-d) followed by o-chloranil oxidation under reflux in toluene. The 4-arylpyridines (5a-i) are obtained predominantly. Having compounds (5a-i) in hand, a convenient method was developed for the synthesis of 2-azafluorenones (7a-f) by using cyclization of 4-arylpyridines (5a-i) with polyphosphoric acid.",

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AU - Shiao, Min Jen

AU - Liu, Kang Hsiuan

AU - Lin, Pen Yuan

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N2 - 3-Substituted 4-arylpyridines (5a-i) were synthesized in good yields by reaction of mixed copper, zinc aryl organometallics (2a-e) with 1-ethoxycarbonyl-pyridinium chlorides (1a-d) followed by o-chloranil oxidation under reflux in toluene. The 4-arylpyridines (5a-i) are obtained predominantly. Having compounds (5a-i) in hand, a convenient method was developed for the synthesis of 2-azafluorenones (7a-f) by using cyclization of 4-arylpyridines (5a-i) with polyphosphoric acid.

AB - 3-Substituted 4-arylpyridines (5a-i) were synthesized in good yields by reaction of mixed copper, zinc aryl organometallics (2a-e) with 1-ethoxycarbonyl-pyridinium chlorides (1a-d) followed by o-chloranil oxidation under reflux in toluene. The 4-arylpyridines (5a-i) are obtained predominantly. Having compounds (5a-i) in hand, a convenient method was developed for the synthesis of 2-azafluorenones (7a-f) by using cyclization of 4-arylpyridines (5a-i) with polyphosphoric acid.

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Syntheses of 2-azafluorenones from 3-substituted 4-arylpyridines

Abstract

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