N-metalated imines by reaction of 1,1-diethoxybut-2-ene with aromatic nitriles, as useful intermediates for the synthesis of substituted pyrimidines and cyclopentenones.
A new approach to the synthesis of pyrimidines and cyclopentenones is described. The method exploits the reactivity of alpha,beta-unsaturated acetals with aromatic nitriles in the presence of the Schlosser's superbase LIC-KOR.
Blangetti
Marco
M
Dipartimento di Chimica Generale e Chimica Organica, Università di Torino, Via P. Giuria, 7, I-10125 Torino, Italy.
Deagostino
Annamaria
A
Prandi
Cristina
C
Zavattaro
Chiara
C
Venturello
Paolo
P
D000080:Acetals / Q000737:chemistry*; D002073:Butanes / Q000737:chemistry*; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D005019:Ethyl Ethers / Q000737:chemistry*; D007097:Imines / Q000138:chemical synthesis* / Q000737:chemistry; D008094:Lithium / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D011188:Potassium / Q000737:chemistry*; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000737:chemistry
C529985:1,1-diethoxybut-2-ene; D000080:Acetals; D002073:Butanes; D003517:Cyclopentanes; D005019:Ethyl Ethers; D007097:Imines; D009570:Nitriles; D011743:Pyrimidines; D008094:Lithium; C013905:cyclopentenone; D011188:Potassium