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 |
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Authors: | Alireza Hasaninejad Nooshin Golzar Mohsen Shekouhy Abdolkarim Zare |
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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) |
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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. |
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Keywords: | Diversity‐oriented synthesis Multicomponent reactions Spiro[indeno[2,1‐b]quinoxaline‐11,4′ ‐pyran]‐2′ ‐amine derivatives Catalysis |
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