Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact: purchase@heterocycles.com

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

Note | Regular issue | Vol 48, No. 1, 1998, pp.145-150
Published online, 1st January, 1970
DOI: 10.3987/COM-97-7934
■ Synthesis of Some New Spiro[indoline-3,2'-(1',2',3',4'-tetrahydroquinoline)]-2,4'-dione Derivatives

Marzoog S. Al-Thebeiti

*Department of Chemistry, Faculty of Applied Sciences, Umm Al-Qura University, Makkah Almukkarramah, P. O. Box 6876, Saudi Arabia

Abstract

Indole-2,3-dione (1) was treated with malonic acid in a mixture of ethanol/pyridine to afford 3-(2-oxoindolinylidine)acetic acid (2), which then reacted with hydrobromic acid to yield 3-bromo-3-(2-oxoindol)acetic acid (3). Compound (3) reacted with aromatic amines to yield 3-arylamino-3-(2-oxoindole)acetic acid derivatives (4a-e). Cyclization of compounds (4a-e) with triflic acid afforded spiro[indoline-3’,2’-(1’,2’,3’,4’-tetrahydroquinoline)]-2,4’-dione derivatives (6a-e). Alkylation of compounds (4a-e) with methyl iodide gave 3-arylmethylamino-2-(1-methyl-2-oxoindole)acetic acid derivatives (5a-e). Cyclization of compounds (5a-e) with triflic acid yielded spiro[indoline-3,2’-(1’,2’,3’,4’-tetrahydroquinoline)]-1,1’-dimethyl-2,4’-dione derivatives (7a-e). Also alkylation of compounds (6a-e) with methyl iodide yielded compounds (7a-e).