ISSN:
0009-2940
Keywords:
Anellated azaphospholes
;
Hantzsch-type [3 + 2] cyclocondensation
;
Chloromethyldichlorophosphane
;
Regioselectivity
;
31P-, 1H-, 13C-NMR spectra
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The [3 + 2] cyclocondensation of 2-amino-1,3-thiazoline, 2-aminopyridines, 2- and 4-aminopyrimidines, 2-aminopyrazine, and 2-aminoquinoline with chloromethyldichlorophosphane in the presence of triethylamine yields regiospecifically 5,6-dihydrothiazolo[2,3-e][1,4,2]diazaphosphole (3), 1,4,2-diazaphospholo[4,5-α]pyridines (12), 1,4,2-diazaphospholo[4,5-α]pyrimidines (15), 1,4,2-diazaphospholo[4,5-e]pyrimidine (17), 1,4,2-diazaphospholo[4,5-α]pyrazine (19), and [1,4,2]diazaphospholo[4,5-α]quinoline (22), respectively. Using 2-amino-1,3-thiazole (4) and 2-aminobenzothiazoles 8, we obtained mixtures of the 1,5- and 4,5-anellated 1,4,2-diazaphospholes 5/6, 9a/10a and 9b/10b, while in the case of the methyl derivative 8c only the [1,4,2]diazaphospholo[5,4-b][1,3]benzothiazole 10c was formed. In the reaction of 2-aminothiazole and 2-aminopyrazine with Chloromethyldichlorophosphane the bis(diazaphospholo)-substituted chloromethylphosphanes 7 and 20 could be detected. The new anellated 1,4,2-diazaphospholes are colorless to pale yellow crystalline moisture-sensitive solids.
Additional Material:
6 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19951280610
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