A new entrant in ketene family: Generation of 2‐(3‐Oxo‐allyl)‐isoindole‐1, 3‐dione and their [4+2] Cycloadditions with 1, 3‐Diazabuta‐1, 3‐dienes. Issue 2 (4th January 2023)

• Record Type: Journal Article
• Authors: Naikoo, Rayees Ahmad; Sharma, Rashmi; Kumar, Rupesh; Bhargava, Gaurav
• Is Part Of: Asian journal of organic chemistry. Volume 12:Issue 2(2023)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2023-01-04
• Subjects: [4+2] Cycloaddition -- Isoindole -- Ketene -- Organic synthons -- Pyrimidinones; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.202200652
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: The manuscript describes a synthetic route for the formation of 5‐(methylisoindole‐1, 3‐dione) pyrimidinones by [4+2] cycloaddition reactions of functionalized 1, 3‐diazabuta‐1, 3‐dienes with 2‐(3‐Oxo‐allyl)‐isoindole‐1, 3‐dione generated in situ from phthaloylalanine and tosyl chloride using triethylamine as a base. The functionalized 5‐(methylisoindole‐1, 3‐dione) pyrimidinones were further explored in the deprotection of amines to afford a variety of 5‐methylamino pyrimidinones. The synthesis of such functionalized pyrimidinones is significant as they have a wide range of pharmacological profiles and are valuable as organic synthons. Mechanistic insights are also proposed for the given synthetic methodology. Abstract : The manuscript describes the formation of 5‐(methylisoindole‐1, 3‐dione) pyrimidinones by [4+2] cycloaddition reactions of functionalized 1, 3‐diazabuta‐1, 3‐dienes with 2‐(3‐Oxo‐allyl)‐isoindole‐1, 3‐dione generated in situ from phthaloylalanine and tosyl chloride using triethylamine as a base. The functionalized 5‐(methylisoindole‐1, 3‐dione) pyrimidinones were further explored in amine deprotection to afford a variety of 5‐methylamino pyrimidinones. The synthesis of such functionalized pyrimidinones is significant as they have a wide range of pharmacological profiles and are valuable as organic synthons.