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Preparation of 1,6-naphthyridine-2,5(1H,6H)-diones

✍ Scribed by Tetsuo Ohta; Hironori Fujisawa; Mitsuru Kawazome; Yasuto Nakai; Isao Furukawa

Publisher
Journal of Heterocyclic Chemistry
Year
2001
Tongue
English
Weight
114 KB
Volume
38
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

Novel method for the synthesis of 3‐acyl‐1,6‐dialkyl‐7‐methyl‐1,6‐naphthyridine‐2,5(1H,6H)‐diones (2) was developed. The reaction of 2‐acyl‐1‐alkylamino‐1‐ethoxyethylenes (1) with acetyl chloride or β‐keto amide 3 with acetyl chloride in the presence of p‐toluenesulfonic acid gave 2 in moderate yield (14‐59% yield).

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✍ Ivanov, Ivo Christov ;Stoyanov, Edmont Vassilev ;Denkova, Pavletta Stoyanova ;Di 📂 Article 📅 1997 🏛 John Wiley and Sons 🌐 English ⚖ 470 KB

## Abstract Vilsmeier formylation of the 4‐amino‐2‐pyridinones 4a–d leads to the formation of the corresponding 3‐carbaldehydes 5a–d (the diformylated product 8 is isolated as a by‐product). A cyclizing Knoevenagel reaction of 5 with CH‐acidic nitriles 6 in the presence of piperidine gives substitu