A new efficient synthesis of imidazolinones and quinazolinone by intramolecular aza-Wittig reaction

✍ Scribed by Hisato Takeuchi; Satoshi Hagiwara; Shoji Eguchi

• Publisher: Elsevier Science
• Year: 1989
• Tongue: French
• Weight: 615 KB
• Volume: 45
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(01)89515-6

✦ Synopsis

A new synthesis of imidazolinones and quinazolinones by intramolecular aza-Wittig reaction is described.

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Readily available azido substituted imides and 12 reacted with triphenylphosphine tributvlnhosoh&e to afford thecorresoondins imidazolinones 1. 7 aZa' quinazolinones 2, 12 via the Staudinger -reaction, intramolecular aza-WXtig reaction. follow& i;y an Recently we have demonstrated that ester carbonyls are reactive in the intramolecular aza-Wittiq reaction 1) , and the new synthesis of oxazoles under mild conditions has been developed utilizing this type of intramolecular imination. In comparison with aldehydes and ketones, ester-, amide-, and imide-carbonyls are generally unreactive in the intermolecular version. Now, we have applied intramolecular aza-Wittig reaction to the imide carbonyl group 2) because it may provide a new convenient route to two-nitrogen containing heterocycles, such as (4H)-imidazolin-5-one 1 and (3H)-quinazolin-4-one 2, that are often involved in some alkaloids 3) and drugs3d' 4'.

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