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Direct introduction of heterocyclic residues into 1,2,4-triazin-5(2H)ones

✍ Scribed by Vladimir L. Rusinov; Grigori V. Zyryanov; Tatjana L. Pilicheva; Oleg N. Chupakhin; Hans Neunhoeffer

Publisher: Journal of Heterocyclic Chemistry
Year: 1997
Tongue: English
Weight: 373 KB
Volume: 34
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570340347

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✦ Synopsis

Abstract

3‐Aryl‐1,2,4‐triazin‐5(2__H__)‐ones 1a‐c react with indoles 2a‐c in trifluoroacetic acid/chloroform or in boiling butanol or acetic acid to give 3‐aryl‐6‐(indolyl‐3)‐1,6‐dihydro‐1,2,4‐triazin‐5(2__H__)‐ones 3a‐g. Oxidation of the dihydro‐1,2,4‐triazin‐5(2__H__)‐ones 3a‐e afforded 6‐(indolyl‐3)‐1,2,4‐triazin‐5(2__H__)‐ones 4a‐e, products of nucleophilic substitution of hydrogen in 1a‐c. Refluxing 1b with N‐methylpyrrote 5b in butanol for an extended time resulted in the formation of 3‐(4‐chlorophenyl)‐6‐(1‐meuiylpyrrolyl‐2)‐1,2,4‐triazin‐5(2__H__)‐one 4h. The reaction of 1a‐c with indoles 2a‐c, pyrroles 5a,b, 1,3‐dimethyl‐2‐phenylpyrazol‐4‐one (8) and aminothiazoles 9a,b in acetic anhydride affords the 1‐acetyl‐3‐aryl‐6‐hetaryl‐1,6‐dihydro‐1,2,4‐triazin‐5(2__H__)‐ones 6a‐s. Reaction of 1a‐c with N‐methyl‐pyrrole 5b in acetic anhydride gives beside the 1:1 addition products 6h‐k also the 2:1 addition products 7a‐c.

📜 SIMILAR VOLUMES

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## Abstract 1,2,4‐Triazin‐5(2__H__)‐ones 1 react as well with phenols, resorinol and its dimethyl ethers, as with dimethyland diethylaniline, yielding 6‐aryl‐1,6‐didydro‐1,2,4‐triazin‐5(2__H__)‐ones 2, 4–8, 12–15. Oxidation of the 1,6‐dihydroadducts 2a,b gives the corresponding 3‐aryl‐6‐hydroxyphen

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ChemInform Abstract: Dihydro-1,2,4-triaz

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Synthesis of Novel Silylated 1,2,4-Triaz

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## Abstract For Abstract see ChemInform Abstract in Full Text.