Simple and efficient access to N-tosyl beta-amino ketones and their conversion into 2,4-disubstituted azetidines.
Treatment of N-tosylaldimines with acetophenone at room temperature in the presence of BF(3).OEt(2) as a catalyst furnished the corresponding N-tosyl beta-amino ketones in high yields (77-86%) within 6-9 h. Subsequent reduction and cyclization of these compounds afforded 2,4-disubstituted N-tosylazetidines, comprising a three-step, high-yielding synthesis starting from aldimines.
Das
Biswanath
B
Organic Chemistry Division-1, Indian Institute of Chemical Technology, Hyderabad 500 007, India. biswanathdas@yahoo.com
Balasubramanyam
Penagaluri
P
Veeranjaneyulu
Boyapati
B
Chinna Reddy
Gandolla
G
D000098:Acetophenones / Q000737:chemistry*; D000586:Amination; D001384:Azetidines / Q000138:chemical synthesis* / Q000737:chemistry; D017605:Bromine Compounds / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D004986:Ether / Q000737:chemistry; D017611:Fluorine Compounds / Q000737:chemistry; D007097:Imines / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry*; D008956:Models, Chemical; D010084:Oxidation-Reduction; D013696:Temperature; D013997:Time Factors; D014105:Tosyl Compounds / Q000138:chemical synthesis / Q000737:chemistry*
D000098:Acetophenones; D001384:Azetidines; D017605:Bromine Compounds; D017611:Fluorine Compounds; D007097:Imines; D007659:Ketones; D014105:Tosyl Compounds; D004986:Ether; C507211:bromine trifluoride; C038699:acetophenone