NAPHTHYRIDINES .1. SYNTHESIS OF SOME 1,7-NAPHTHYRIDINES
NAPHTHYRIDINES .1. SYNTHESIS OF SOME 1,7-NAPHTHYRIDINES
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DOI：
10.1021/ja01614a023
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发表时间：
1955-01-01
影响因子：
15
通讯作者：
KRIEGER, AL
中科院分区：
文献类型：
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作者：
BAUMGARTEN, HE;KRIEGER, AL
用二氧化硒氧化3-硝基-4-甲基吡啶得到3-硝基-4-吡啶甲醛。醛与对甲苯胺缩合得到N-(3-硝基-4-吡啶亚甲基)-/>-甲苯胺(III)，将其还原为N-(3-氨基-4-吡啶亚甲基)-/>-甲苯胺(IV)。后者与苯乙酮和环己酮缩合分别得到2-苯基-1,7-萘啶和2,10-二氮杂-5,6,7,8-四氢蒽(VI)。 3-硝基-4-吡啶甲醛与丙二酸反应得到d-(3-硝基-4-吡啶基)-丙烯酸，将其还原为5-(3-氨基-4-吡啶基)-丙烯酸，后者环化为2-羟基-1,7-萘啶。 3-高喹啉酸的铵盐的融合得到6,8-二羟基-1,7-萘啶。
Oxidation of 3-nitro-4-picoline with selenium dioxide gave 3-nitro-4-pyridinecarboxaldehyde. Condensation of the aldehyde with f>-toluidine gave N-(3-nitro-4-picolylidene)-/>-toluidine (III), which was reduced to N-(3-amino-4-picolylidene)-/>-toluidine (IV). Condensation of the latter with acetophenone and with cyclohexanone gave 2-phenyl-l, 7-naphthyridine and 2, 10-diaza-5, 6, 7, 8-tetrahydroanthracene (VI), respectively. Reaction of 3-nitro-4-pyridinecarboxaldehyde with malonic acid gave d-(3-nitro-4-pyridyl)-acrylic acid, which was reduced to 5-(3-amino-4-pyridyl)-acrylic acid, and the latter was cyclized to 2-hydroxy-l, 7-naphthyridine. Fusion of the ammonium salt of/3-homoquinolinic acidgave 6, 8-dihydroxy-l, 7-naphthyridine.