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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
Authors:Alireza Hasaninejad  Nooshin Golzar  Mohsen Shekouhy  Abdolkarim Zare
Affiliation:1. Department of Chemistry, Faculty of Sciences, Persian Gulf University, Bushehr 75169, Iran, (phone/fax: +98‐771‐4541494);2. Department of Chemistry, Payame Noor University, P.O. Box 19395‐3697, Tehran, Iran, (phone/fax: +98‐771‐5559486)
Abstract:
A sequential one‐pot four‐component reaction for the efficient synthesis of novel 2′‐aminospiro[11H‐indeno[1,2‐b]quinoxaline‐11,4′‐[4H]pyran] derivatives 5 in the presence of AcONH4 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[11H‐indeno[1,2‐b]quinoxaline‐11,4′‐[4H]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.
Keywords:Diversity‐oriented synthesis  Multicomponent reactions  Spiro[indeno[2,1‐b]quinoxaline‐11,4′  ‐pyran]‐2′  ‐amine derivatives  Catalysis
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