ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The readily available 5-nitrospiro[2H-benzimidazole-2,1′-cyclohexane] (1) was converted into the carbonitrile 5 and the 4-phenylthio derivative 4. The NO2 or the PhS substituents in 4 could be replaced regiospecifically by reaction with Me3SiN3 or NaN3, respectively. The 5-azido derivative 8, resulting from NO2-group replacement was made to cyclize photolytically to give the angular spiro[cyclohexane-imidazophenothiazine] 18. The azide 9 obtained from the PhS replacement in 4 cyclized spontaneously to give the angular spiro[cyclohexane-imidazobenzoxadiazole] 10 which, on reductive hydrolysis, furnished benzofurazan-4,5-diamine 14. The diamine 14 was converted by conventional methods into a imidazobenzoxadiazole 15, oxadiazoioquinoxaline 16, and selenadiazoloxadiazole 17. The carbonitrile 5 was converted, in simple steps, into the ‘stretched-out’, angular pteridine and purine analogues, 25 and 28, respectively.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19900730417
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