ISSN:
0170-2041
Keywords:
(Tosylamino)alkanes
;
Piperazine, 2-benzoyl-
;
Norrish-II reaction
;
Photocyclisation
;
2,5-Diazabicyclo[2.2.1]heptane
;
3,6-Diazabicyclo[3.2.1]octane
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Photochemistry of Amino Ketones, 141). - Synthesis and Transannular Photocyclisation of 2-Benzoyl-1,4-bis-(tosyl)piperazines1,1-Dialkyl-1,2-bis(tosylamino)ethanes 4 are prepared in a three-step reaction starting with dialkyl ketones 1. With strong bases in dimethylformamide compounds 4 react regioselectively with 1,2-dibromoalkyl phenyl ketones 5 to afford the 2-benzoyl-1,4-bis(tosyl)piperazines 6. On irradiation (≥ 300 nm) the piperazines 6a, b, f, g, without substituents in position 6, undergo Norrish-II cleavage yielding open-chain products. Depending on the ring conformations the 2,2-dialkylpiperazines 6c, d, e form diazabicycloalkanes 10 and 11 on irradiation.
Additional Material:
4 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.1991199101170
