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An efficient strategy for the regioselective synthesis of 3-phosphorylated-1-aminopyrroles from β-hydrazono phosphine oxides and phosphonates

✍ Scribed by Francisco Palacios; Domitila Aparicio; Jesús M. de los Santos

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
837 KB
Volume
55
Category
Article
ISSN
0040-4020

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✦ Synopsis

Abstmt: An easy strategy for the synthesis of 1-aminopyrroles substituted with a phosphine oxide or phosphonate group in the 3-position is described. The key step is the 1,4-conjugate addition of the enamine to the 4-phosphorylated 1,2-diazabuta-1,3-diene 3 and heterocyclisation to give substituted laminopyrroles 9. Basic hydrolysis of pyrroles 9 afforded 3-phosphinoyl-1-aminopyrroles 11. Similarly, substituted 3-phosphinoyl-1-aminopyrroles 10, can also be obtained from acetylacetone and 1,2-diazabuta-1.3-diene 3. 0

📜 SIMILAR VOLUMES

An efficient and general strategy for th
An efficient and general strategy for the synthesis of 4-phosphorylated pyrazoles from β-hydrazono phosphine oxides
✍ Francisco Palacios; Domitila Aparicio; Jesús M. de los Santos 📂 Article 📅 1996 🏛 Elsevier Science 🌐 French ⚖ 630 KB

A simple and efficient synthesis of aminopyrazoles substituted with a phospkino oxide and sulphide groups in the 4-position 1 is described. The key step is a regioselective addition of fithiated [~hydrazonophosphine oxides 2 to isocyanates and isothiocyanates to give functionalized amides 3 and 7. S