Four‐Component Regio‐ and Diastereoselective Synthesis of Pyrrolizidines Incorporating Spiro‐Oxindole/Indanedione via 1,3‐Dipolar Cycloaddition Reaction of Azomethine Ylides | Zendy

Alizadeh Abdolali | Zendy; Roosta Atefeh | Zendy; Halvagar Mohammadreza | Zendy

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Four‐Component Regio‐ and Diastereoselective Synthesis of Pyrrolizidines Incorporating Spiro‐Oxindole/Indanedione via 1,3‐Dipolar Cycloaddition Reaction of Azomethine Ylides

Author(s) -

Alizadeh Abdolali,

Roosta Atefeh,

Halvagar Mohammadreza

Publication year - 2019

Publication title -

chemistryselect

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.437

H-Index - 34

ISSN - 2365-6549

DOI - 10.1002/slct.201803418

Subject(s) - isatin , pyrrolizidine , ninhydrin , chemistry , oxindole , cycloaddition , 1,3 dipolar cycloaddition , regioselectivity , component (thermodynamics) , azomethine ylide , combinatorial chemistry , organic chemistry , stereochemistry , amino acid , catalysis , biochemistry , physics , thermodynamics

The present investigation reports an easy regio‐ and diastereoselective access to a library of diverse polycyclic pyrrolizidine fused spiro‐1,3‐indandione/oxindole derivatives through a one‐pot sequential four‐component reactions of 4‐oxo‐4 H ‐chromene‐3‐carbaldehyde/2‐chloroquinoline‐3‐carbaldehyde, 1‐phenyl‐2‐(1,1,1‐triphenyl‐ λ 5 ‐phosphanylidene)ethan‐1‐one, ninhydrin or isatin, and L‐proline in EtOH at room temperature. This protocol features excellent chemical yields, high diastereoselectivity and operational simplicity.

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