ISSN:
0947-3440
Keywords:
Medium-sized rings
;
Cyclizations
;
Alkynes
;
Heterocycles
;
Multicomponent reactions
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The preparation of N,N′-dialkyl- and N,N′-diaryl-1,6-diazacyclodeca-3,8-diynes was achieved by reaction of alkyl- or arylamines with 1,4-dihalobut-2-yne under dilution conditions in yields of 5-15%. The compounds synthesized by this procedure were the N,N′-dimethyl (2b), N,N′-diethyl (2c), N,N′-diisopropyl (2d), N,N′-di-tert-butyl (2e), N,N′-dicyclohexyl (2f), N,N′-diphenyl (2g), and N,N′-di-p-tolyl (2h) derivatives. The parent compound 2a was obtained in ca. 40% yield by heating 2d with α-chloroethylchloroformate (20). Using 1,9-dibromonona-2,7-diyne (10) and methylamine or isopropylamine, respectively, the corresponding N-alkyl-1-azacyclodeca-3,8-diynes 4b and 4d were synthesized under dilution conditions. By heating 4d with 20 we obtained 1-azacyclodeca-3,8-diyne (4a). As side products of the cyclization reactions the trimers 18 and tetramers 12 and 19 were isolated and characterized. N-methyl-1-azacycloundeca-3,9-diyne (14b) was prepared by reaction of 1,10-dibromodeca-3,8-diyne (13) with methylamine.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199719971013
