Retro-Ene Reactions in Heterocyclic Synthesis. Part 4. A New Synthetic Method for 6-Hydroxypyrimidin-4(3H)-ones and 1,3,5-Triazine-2,4(1H,3H)-diones. -Reaction of benzamidines (I) with substituted malonates (II) and imidodicarboxylate (IV) provides an efficient access to 6-hydroxypyrimidinones (III
Retro-ene reactions in heterocyclic synthesis. IV. A new synthetic method for 6-hydroxypyrimidin-4(3H)-ones and 1,3,5-triazine-2,4(1H,3H)-diones
✍ Scribed by Kunio Ito; Shingo Miyajima
- Publisher
- Journal of Heterocyclic Chemistry
- Year
- 1999
- Tongue
- English
- Weight
- 210 KB
- Volume
- 36
- Category
- Article
- ISSN
- 0022-152X
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✦ Synopsis
(N) - (t)-Butylbenzamidines 1 reacted with diphenyl phenylmalonate or diphenyl methylmalonate to give 6-hydroxypyrimidin-4(3H)-ones 4 or 5 . Amidines 1 on reaction with diphenyl imidodicarboxylate afforded (1,3,5)-triazine- (2,4(1 H, 3 H))-diones 8 .
📜 SIMILAR VOLUMES
## Abstract magnified image __N__‐__t__‐Butylamidines **1** on heating with diphenyl carbonate (**2**) at 150‐180° gave the 1,3,5‐triazine‐2,4(1__H__,3__H__)‐dione derivatives **5**. Acylation of amidines **1** and cyclocondensation of the resulting carbamates **3** gave [1,3,5,7]tetrazocine‐2,6‐d
## Abstract Methyl (__E__)‐4,4‐dimethyl‐5‐oxo‐2‐pentenoate (1, X = O) reacted with 1,2‐ or 1,3‐aminoalcohols 3 to yield oxazolidines 4a‐c or tetrahydro‐1,3‐oxazines 4d,e. The corresponding imino ester 1 (X = NBu‐__t__) also gave 4 on reaction with 3. Compounds 4 on heating at 230° yielded 4,5‐dihyd