Regio- and diastereoselective dialkylation of (4S)-2,4-dimethyl-2,4-dihydro-1H-pirazino[2,1-b]quinazoline-3,6-dione
✍ Scribed by Sonsoles Martín-Santamaría; Modesta Espada; Carmen Avendaño
- Book ID
- 104208193
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 400 KB
- Volume
- 53
- Category
- Article
- ISSN
- 0040-4020
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✦ Synopsis
Abstmctz Dialkylation of the title compound occurs regioselectively at C-l. Addition of N,N'-diiethyl-NJ'-propylene urea (DMFV) permits the one-pot synthesis of I,l-dialkylation products in good yields. The asymmetric induction of the stereogenic C-4 center directs the first and the second alkylation steps.
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The enamine character of the CH2-C(lla)=N(ll) fragment in the title compounds was studied. Congxatmds I gave l-dimethylaminomethylene products $ after Vilsmeier reaction. The l-formyl derivatives, obtained by alkaline hydrolysis of 5, were isolated as enol tautome~s and were vea'y unstable in acid m