Premium
Synthesis of ( E )‐3‐(2‐Oxo‐2‐arylethylidene)indolin‐2‐ones through Alkyne Carbonyl Metathesis and Their Stereospecific Application towards Spiro‐oxindolopyrrolizidine Scaffolds
Author(s) -
Basu Soumyadip,
Mukhopadhyay Chhanda
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701606
Subject(s) - chemistry , regioselectivity , stereospecificity , alkyne , indoline , catalysis , metathesis , combinatorial chemistry , atom economy , organic chemistry , polymerization , polymer
An iron‐salt catalyzed, atom economic, unfamiliar type of alkyne carbonyl metathesis strategy has been developed by using isatins and acetylenes for the regioselective synthesis of ( E )‐3‐(2‐oxo‐2‐arylethylidene)indolin‐2‐one derivatives, which has been further utilized to develop a catalyst‐free methodology for the synthesis of biologically active spiro‐oxindolopyrrolizidine scaffolds in a highly regio‐ and stereospecific manner by reacting with l ‐proline and aldehydes. Both methods are acceptable towards various functionalities that include electron‐donating and electron‐accepting groups at the ortho ‐, meta ‐ and para ‐positions. This protocol provides an environmentally friendly reaction methodology for the synthesis of a series of (1′ S ,2′ R ,3′ R ,7a′ R )‐1′,3′,5′,6′,7′,7a′‐hexahydrospiro[indoline‐3,2′‐pyrrolizin]‐2‐ones.