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A comparative study of conventional conditions versus microwave irradiation for the preparation of novel 1,2-dihydro-2-imino-7-methyl-1,6(6H)-naphthyridin-5-ones

✍ Scribed by Dieter Heber; Edmont V. Stoyanov

Publisher
Journal of Heterocyclic Chemistry
Year
2000
Tongue
English
Weight
234 KB
Volume
37
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

The synthesis of novel 1,6‐naphthyridines 6 with potential activity against tuberculosis is described using the reaction sequence 2←4←6. Depending on the ring N‐substitution of the 4‐alkylamino‐6‐methyl‐2(1__H__)‐pyridones 1 and 2 the electrophilic attack of the Vilsmeier reagent gives rise to the formation of the exocyclic N‐formyl derivatives 3 from 1 and the corresponding 3‐carbaldehydes 4 from 2. 1,2‐Dihydro‐2‐imino‐7‐methyl‐1,6(6__H__)‐naphthyridin‐5‐ones 6a‐j are prepared by the Knoevenagel reaction of 4 with CH‐acidic nitriles 5. These reactions are carried out using a comparative study of conventional conditions (room temperature or reflux) versus microwave irradiation.

📜 SIMILAR VOLUMES

Synthesis of Substituted 1,2-Dihydro-2-i
Synthesis of Substituted 1,2-Dihydro-2-imino-7-methyl-1,6(6H)-naphthyridin-5-ones
✍ 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