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Microwave‐assisted One‐pot, Three‐component Regiospecific and Sterospecific Synthesis of Spiro Indanone Pyrrolidine/Piperidine Fused Nitrochromene Derivatives Through 1,3‐Dipolar Cycloaddition Reactions
Author(s) -
Nayak Sabita,
Panda Pravati,
Mohapatra Seetaram,
Raiguru Bishnuprasad,
Baral Nilofar
Publication year - 2019
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.3534
Subject(s) - chemistry , cycloaddition , pyrrolidine , piperidine , 1,3 dipolar cycloaddition , azomethine ylide , pipecolic acid , molecule , stereochemistry , organic chemistry , amino acid , biochemistry , catalysis
A simple, straightforward, and versatile protocol for the synthesis of spiro indanone pyrrolidine/piperidine fused nitrochromene derivatives is described. The synthesis of a new series of spirocyclic molecules has been expediently accomplished via a one‐pot, three component 1,3‐dipolar cycloaddition reaction. 2‐Phenyl‐nitrochromene dipolarophiles were reacted with azomethine ylides, generated in situ by the condensation of dicarbonyl compound indane‐1,3‐dione and secondary amino acid (L‐proline/pipecolic acid), to produce the corresponding cycloadducts in good yields (85–90%) under classical as well as under microwave irradiation. The cycloaddition reaction was found to be highly regiospecific and diasterospecific. The regiochemical and sterochemical outcome of the cycloaddition reaction is ascertained by 2D NMR (COSY and NOESY) studies.