Methanetricarboxylates as key reagents for the simple preparation of heteroarylcarboxamides with potential biological activity. Part 1 reaction of methanetricarboxylates with indoline and 1,2,3,4-tetrahydroquinoline

✍ Scribed by Alexander Kutyrev; Thomas Kappe

• Publisher: Journal of Heterocyclic Chemistry
• Year: 1997
• Tongue: English
• Weight: 231 KB
• Volume: 34
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570340340

✦ Synopsis

Abstract

The reaction of methanetricarboxylates 2a,b with indoline as well as 1,2,3,4‐tetrahydroquinoline yields tricyclic 4‐hydroxy‐2(1__H__)‐quinolones with an ester group in position 3 (3, 8a,b). These heterocyclic esters condense with primary aliphatic, aromatic, and heteroaromatic amines to give the corresponding amides 5a‐e and 10a‐t.