Regioselective ring expansion of 2,4-diiminoazetidines via cleavage of C-N and C(sp3)-H bonds: efficient construction of 2,3-dihydropyrimidinesulfonamides.
A highly regioselective base-mediated ring expansion of 2,4-diiminoazetidines via cleavage of C-N and C(sp(3))-H bonds is achieved for the first time to afford efficiently 2,3-dihydropyrimidinesulfonamides. The mechanism of the ring expansion via tandem 4π electrocyclic ring-opening/1,5-H shift/6π electrocyclic ring-closing is well confirmed by the trapping experiments of two key intermediates and deuterium labeling studies.
Beijing National Laboratory for Molecular Sciences, and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemisstry, Peking University, Beijing 100871, China.
Yang
Y
Wang
Yue
Y
Chi
Wen-Xiong
WX
Zhang
Zhenfeng
Z
Xi
D001384:Azetidines / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D002621:Chemistry / Q000379:methods*; D003500:Cyclization; D004583:Electrons; D006859:Hydrogen / Q000737:chemistry*; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008956:Models, Chemical; D009584:Nitrogen / Q000737:chemistry*; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry
D001384:Azetidines; D013449:Sulfonamides; D002244:Carbon; D006859:Hydrogen; D009584:Nitrogen