Synthesis and reactions of 10,10-dimethyl-10H-pyrido[1,2-a]indol-6-ones

✍ Scribed by Thomas Kappe; Franz Frühwirth; Peter Roschger; Brigitte Jocham; Jenny Kremsner; Wolfgang Stadlbauer

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2002
• Tongue: English
• Weight: 70 KB
• Volume: 39
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570390224

✦ Synopsis

Abstract

Cyclocondensation of 2,3,3‐trimefhyl‐3__H__‐indoles 2 with malonates 3 gives 8‐hydroxy‐10,10‐dimefhyl‐10__H__‐pyrido[1,2‐a]indol‐6‐ones 4, which were halogenated in position 7, 8 and 9 with sulfuryl chloride, bromine or phosphoroxychloride to give the corresponding halo‐10,10‐dimethyl‐10__H__‐pyrido[1,2‐a]indoles 5, 6, 7 and 8. Amination affords the 8‐amino‐10,10‐dimethyl‐10__H__‐pyrido[1,2‐a]indol‐6‐one 9. Nitration gives either the 10,10‐dimethyl‐7‐nitro‐10__H__‐pyrido[1,2‐a]indoles 10 or 10,10‐dimethyl‐7‐hydroxy‐10__H__‐pyrido[1,2‐a]indoles 11, depending on the conditions.