Aqueous N-heterocyclization of primary amines and hydrazines with dihalides: microwave-assisted syntheses of N-azacycloalkanes, isoindole, pyrazole, pyrazolidine, and phthalazine derivatives.
[reactions: see text] The synthesis of nitrogen-containing heterocycles from alkyl dihalides (ditosylates) and primary amines and hydrazines via a simple and efficient cyclocondensation in an alkaline aqueous medium that occurs under microwave irradiation is described. This improved greener synthetic methodology provides a simple and straightforward one-pot approach to the synthesis of a variety of heterocycles, such as substituted azetidines, pyrrolidines, piperidines, azepanes, N-substituted 2,3-dihydro-1H-isoindoles, 4,5-dihydropyrazoles, pyrazolidines, and 1,2-dihydrophthalazines.
Ju
Yuhong
Y
Clean Processes Branch, Sustainable Technology Division, National Risk Management Research Laboratory, U.S. Environmental Protection Agency, 26 West Martin Luther King Drive, MS 443, Cincinnati, Ohio 45268, USA. Ju.Yuhong@epa.gov
Varma
Rajender S
RS
D000473:Alkanes / Q000138:chemical synthesis / Q000737:chemistry*; D000478:Alkylation; D000588:Amines / Q000737:chemistry*; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D006358:Hot Temperature; D006834:Hydrazines / Q000737:chemistry*; D006859:Hydrogen / Q000737:chemistry; D007211:Indoles / Q000737:chemistry*; D007536:Isomerism; D008872:Microwaves; D015394:Molecular Structure; D008970:Molecular Weight; D009584:Nitrogen / Q000737:chemistry; D010793:Phthalazines / Q000737:chemistry*; D011720:Pyrazoles / Q000737:chemistry*
D000473:Alkanes; D000588:Amines; D001372:Aza Compounds; D006834:Hydrazines; D007211:Indoles; D010793:Phthalazines; D011720:Pyrazoles; C031280:pyrazole; D006859:Hydrogen; C043388:phthalazine; D009584:Nitrogen