Diversity-Oriented Synthesis of Novel 2′-Aminospiro[11H-indeno[1,2-b]quinoxaline-11,4′-[4H]pyran] Derivatives via a One-Pot Four-Component Reaction

✍ Scribed by Alireza Hasaninejad; Nooshin Golzar; Mohsen Shekouhy; Abdolkarim Zare

• Publisher: John Wiley and Sons
• Year: 2011
• Tongue: German
• Weight: 174 KB
• Volume: 94
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.201100201

✦ Synopsis

Abstract

A sequential one‐pot four‐component reaction for the efficient synthesis of novel 2′‐aminospiro[11__H__‐indeno[1,2‐b]quinoxaline‐11,4′‐[4__H__]pyran] derivatives 5 in the presence of AcONH~4~ as a neutral, inexpensive, and dually activating catalyst is described (Scheme 1). The syntheses are achieved by reacting ninhydrin (1) with benzene‐1,2‐diamines 2 to give indenoquinoxalines, which are trapped in situ by malono derivatives 2 and various α‐methylenecarbonyl compounds 4 through cyclization, providing the multifunctionalized 2′‐aminospiro[11__H__‐indeno[1,2‐b]quinoxaline‐11,4′‐[4__H__]pyran] analogs 5. This chemistry provides an efficient and promising synthetic way of proceeding for the diversity‐oriented construction of the spiro[indenoquinoxalino‐pyran] skeleton.