One‐Pot Synthesis of Functionalized Isoindolinones and Their Bis(isoindolinone)ethane Derivatives. Issue 47 (15th December 2022)

• Record Type: Journal Article
• Authors: Purohit, Deepak; Singh Rawat, Kundan; Parveen, Sajiya; Prakash Vats, Ravi; Prakash Sharma, Chandra; Goel, Atul
• Is Part Of: European journal of organic chemistry. Volume 2022:Issue 47(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-12-15
• Subjects: Isoindolinones -- Hydroxyisoindolin-1-one -- β-hydroxyketone -- Dimroth rearrangement -- Bis(isoindolinone)ethane; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202201128
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Highly efficient one‐pot synthesis of a series of substituted 3‐methylene‐isoindolinones (3 a –x ), bis(isoindolinone)ethanes (4 a –d ) and 3‐hydroxy‐isoindolinones (6 a –h ) derivatives is portrayed from easily accessible starting materials such as 2‐cyanobenzaldehydes (1 a –h ) and different aryl/heteroaryl methyl ketones (2 a –k ). The structure of Z‐isomer of 3‐methylene‐isoindolinone 3 x was confirmed by single crystal X‐ray analysis. The reaction mechanism studies by control experiments and using O 18 ‐labelled water revealed that the reaction was initiated by attack of a conjugate base of aryl/heteroaryl methyl ketones (2 a –k ) to aldehyde group of 1 a –h followed by intramolecular oxidative cyclization involving nitrile functionality to furnish isoindolinone derivatives in good to excellent yields. Abstract : A one‐pot synthesis of a series of substituted 3‐methylene‐isoindolinones (3 a –x ), bis(isoindolinone)ethanes (4 a –d ) and 3‐hydroxy‐isoindolinones (6 a –h ) derivatives is described.