A Novel, One-Pot Four-Component Route to 2′-Thioxo-2′,3′-dihydrospiro[indole-3,6′-[1,3]thiazin]-2-one Derivatives

✍ Scribed by Abdolali Alizadeh; Javad Mokhtari

• Book ID: 102257564
• Publisher: John Wiley and Sons
• Year: 2011
• Tongue: German
• Weight: 145 KB
• Volume: 94
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.201000419

✦ Synopsis

Abstract

An efficient route to 2′,3′‐dihydro‐2′‐thioxospiro[indole‐3,6′‐[1,3]thiazin]‐2(1__H__)‐one derivatives is described. It involves the reaction of isatine, 1‐phenyl‐2‐(1,1,1‐triphenyl‐λ^5^‐phosphanylidene)ethan‐1‐one, and different amines in the presence of CS~2~ in dry MeOH at reflux (Scheme 1). The alkyl carbamodithioate, which results from the addition of the amine to CS~2~, is added to the α,β‐unsaturated ketone, resulting from the reaction between 1‐phenyl‐2‐(1,1,1‐triphenyl‐λ^5^‐phosphanylidene)ethan‐1‐one and isatine, to produce the 3′‐alkyl‐2′,3′‐dihydro‐4′‐phenyl‐2′‐thioxospiro[indole‐3,6′‐[1,3]thiazin]‐2(1__H__)‐one derivatives in excellent yields (Scheme 2). Their structures were corroborated spectroscopically (IR, ^1^H‐ and ^13^C‐NMR, and EI‐MS) and by elemental analyses.