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Retro-ene reactions in heterocyclic synthesis. v. a novel synthetic method for 1,3,5-triazine-2,4(1H,3H)-diones

✍ Scribed by The Late Kunio Ito; Chiharu Sekiguchi; Asuka Wakai Hiroyuki Miida; Shogo Ihara

Publisher
Journal of Heterocyclic Chemistry
Year
2007
Tongue
English
Weight
223 KB
Volume
44
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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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‐dione derivatives 4, and subsequent retro‐ene reaction and ring contraction afforded triazine derivatives 5.

📜 SIMILAR VOLUMES

Retro-ene reactions in heterocyclic synt
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
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\(N\) - \(t\)-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 .

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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

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✍ Kunio Ito; Shingo Miyajima 📂 Article 📅 1997 🏛 Journal of Heterocyclic Chemistry 🌐 English ⚖ 198 KB

## 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