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

作者：Hasaninejad Alireza^*; Golzar Nooshin; Shekouhy Mohsen; Zare Abdolkarim

来源：Helvetica Chimica Acta, 2011, 94(12): 2289-2294.

DOI：10.1002/hlca.201100201

• Diversity-oriented synthesis
• Multicomponent reactions
• Spiro[indeno[2
• 1-b]quinoxaline-11
• 4'-pyran]-2'-amine derivatives
• Catalysis

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 a-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.

• 出版日期2011-12