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Diversity‐Oriented Synthesis of Novel 2′‐Aminospiro[11 H ‐indeno[1,2‐ b ]quinoxaline‐11,4′‐[4 H ]pyran] Derivatives via a One‐Pot Four‐Component Reaction
Author(s) -
Hasaninejad Alireza,
Golzar Nooshin,
Shekouhy Mohsen,
Zare Abdolkarim
Publication year - 2011
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201100201
Subject(s) - quinoxaline , chemistry , pyran , ninhydrin , one pot synthesis , catalysis , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , biochemistry , amino acid
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.