Synthesis of (E)‐3‐(2‐Oxo‐2‐arylethylidene)indolin‐2‐ones through Alkyne Carbonyl Metathesis and Their Stereospecific Application towards Spiro‐oxindolopyrrolizidine Scaffolds. Issue 12 (30th March 2018)

• Record Type: Journal Article
• Authors: Basu, Soumyadip; Mukhopadhyay, Chhanda
• Is Part Of: European journal of organic chemistry. Issue 12(2018)
• Page Start: 1496
• Page End: 1506
• Publication Date: 2018-03-30
• Subjects: Synthetic methods -- Spiro compounds -- Metathesis -- Metal‐salt catalysis -- Diastereoselectivity -- Multicomponent reactions; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201701606
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : 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 withl ‐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. Abstract : A transition metal salt catalyzed alkyne carbonyl metathesis followed by a multicomponent protocol to synthesize highly substituted new (1′ S, 2′ R, 3′ R, 7a′ R )‐1′, 3′, 5′, 6′, 7′, 7a′‐hexahydrospiro[indoline‐3, 2′‐pyrrolizin]‐2‐ones. A total of 39 compounds were synthesized by an interesting combination of metal‐salt catalysis and a multicomponent strategy.