An Efficient Synthesis of Spiro‐oxindole Derivatives by Three‐Component Reactions in Water. Issue 4 (April 2015)

• Record Type: Journal Article
• Authors: Alizadeh, Abdolali; Moafi, Leila
• Is Part Of: Helvetica chimica acta. Volume 98:Issue 4(2015:Apr.)
• Page Start: 546
• Page End: 551
• Publication Date: 2015-04
• Subjects: Chemistry -- Periodicals; Chemistry, Analytical -- periodicals; Chimie -- Périodiques; 540
• DOI: 10.1002/hlca.201400263
• Languages: English
• ISSNs: 0018-019X

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>An efficient synthesis of (3<italic>S</italic>)‐1, 1′, 2, 2′, 3′, 4′, 6′, 7′‐octahydro‐9′‐nitro‐2, 6′‐dioxospiro[3<italic>H</italic>‐indole‐3, 8′‐[8<italic>H</italic>]pyrido[1, 2‐<italic>a</italic>]pyrimidine]‐7′‐carbonitrile is achieved <italic>via</italic> a three‐component reaction of isatin, ethyl cyanoacetate, and 1, 2, 3, 4, 5, 6‐hexahydro‐2‐(nitromethylidene)pyrimidine. The present method does not involve any hazardous organic solvents or catalysts. Also the synthesis of ethyl 6′‐amino‐1, 1′, 2, 2′, 3′, 4′‐hexahydro‐9′‐nitro‐2‐oxospiro[3<italic>H</italic>‐indole‐3, 8′‐[8<italic>H</italic>]pyrido[1, 2‐<italic>a</italic>]pyrimidine]‐7′‐carboxylates in high yields, at reflux, using a catalytic amount of piperidine, is described. The structures were confirmed spectroscopically (IR, ¹H‐ and ¹³C‐NMR, and EI‐MS data) and by elemental analyses. A plausible mechanism for this reaction is proposed (<italic>Scheme 2</italic>).</p> </abstract>