One pot,three component synthesis of spiroindenoquinoxaline pyrrolidine fused nitrochromene derivatives following 1,3-dipolar cycloaddition |
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Authors: | Sabita Nayak Priyabrata Pattanaik Deepak Ranjan Mishra Pravati Panda Bishnuprasad Raiguru |
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Affiliation: | Department of Chemistry, Ravenshaw University, Cuttack, Odisha, India |
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Abstract: | An expedient one-pot sequential three-component synthesis of a series of diverse spiroindenoquinoxaline pyrrolidine fused nitrochromene derivatives following 1,3-dipolar cycloaddition of azomethine ylides generated in situ by the condensation of indenoquinoxalone and α-amino acids (L-proline and L-phenyl alanine) with 3-nitrochromenes as dipolarophile under classical as well as microwave irradiation is described. The protocol provides a mild reaction condition, high yield of the products, high regioselectivity, and operational simplicity to assemble complex structural entity in a single operation with good to excellent yield. The regio and stereochemical outcome of the cycloaddition reaction is ascertained by spectroscopic and single crystal X-ray analysis. |
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Keywords: | Azomethine ylides 1,3-dipolar cycloaddition indenoquinoxaline multicomponent reactions spiro compounds nitrogen heterocycles 3-nitro-2H-chromene |
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