ChemInform Abstract: Activation of the 4-Oxo Function in 1-Alkyl-1,4-dihydro-4-oxoquinoline-3-carboxylic Acids with Thionyl Chloride.

✍ Scribed by T. VAN ES; B. STASKUN

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 33 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199907159

✦ Synopsis

Activation of the 4-Oxo Function in 1-Alkyl-1,4-dihydro-4oxoquinoline-3-carboxylic Acids with Thionyl Chloride.

-Treatment of the title acids (I) with SOCl 2 and subsequently with amines (II) affords the hitherto unknown 4-imino acids (III) and/or the 4-imino amides (IV) instead of the expected 4-oxo amides. It is shown that the selectivity to imino amides (IV) is higher using neat amines in large excess. Sometimes, an additional substitution of the 7-fluoro by amino group is observed. An acid chloride-hydrogen chloride complex intermediate is proposed. -( VAN ES,