Intramolecular formal [4 + 2] cycloaddition of nitriles with amides triggered by TMSOTf/Et3N: highly efficient construction of pyrrolo[1,2-a]pyrimidin-4(6H)-ones.
By treatment with TMSOTf/Et3N, N-(2-cyanoarylmethyl)-substituted acrylamides or beta-ketoamides underwent N-addition cascades under mild conditions to afford the corresponding pyrrolo[1,2-a]pyrimidin-4(6H)-ones as the formal [4 + 2] cycloaddition products in high yields.
Liu
Feng
F
Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. China.
Li
Chaozhong
C
D000577:Amides / Q000737:chemistry*; D003500:Cyclization; D005021:Ethylamines / Q000737:chemistry*; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D011744:Pyrimidinones / Q000138:chemical synthesis* / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
D000577:Amides; D005021:Ethylamines; D008698:Mesylates; D009570:Nitriles; D011744:Pyrimidinones; D011758:Pyrroles; D014297:Trimethylsilyl Compounds; C545230:pyrrolo(1,2-a)pyrimidin-4(6H)-one; C053353:trimethylsilyl trifluoromethanesulfonate; C016162:triethylamine