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A New Four-Component Reaction for the Synthesis of Spiro[4H-indeno[1,2-b]pyridine-4,3′-[3H]indoles]

✍ Scribed by Afsaneh Feiz; Ghazaleh Imani Shakibaei; Zahra Yasaei; Hamid Reza Khavasi; Ayoob Bazgir

Publisher
John Wiley and Sons
Year
2011
Tongue
German
Weight
240 KB
Volume
94
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

A new four‐component synthesis of spiro[4__H__‐indeno[1,2‐b]pyridine‐4,3′‐[3__H__]indoles] and spiro[acenaphthylene‐1(2__H__),4′‐[4__H__‐indeno[1,2‐b]pyridines] by the reaction of indane‐1,3‐dione, 1,3‐dicarbonyl compounds, isatins (=1__H__‐indole‐2,3‐diones) or acenaphthylene‐1,2‐dione, and AcONH~4~ in refluxing toluene in the presence of a catalytic amount of pyridine is reported.

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m. p.=248-250GC (dec.; from methanol); [.ID= -129.' (DMSO, c = 1.00); 'H-NMR (D6-DMSO); t=4.13 and 4.18 (s, I-H+l'-H and s, 2 2-benzyl-H, or vice versa); MS: 520 (M+)]. The amino ketone ( 8 ) is probably first formed, being later aromatized by dimerization and air oxidation to yield ( 9 ) . The firs