ISSN:
0021-8383
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
About the Reaction between Hydrazines and Aminohydroxy-hydrobenzoxazol. Synthesis of AzoolefinesBy the reaction of 1-hydroxy-2-oxocyclohexane-carboxamide (1) with cyanamide 2-amino-7a-carbamoyl-3a-hydroxy-3a,4a,5,6,7,7a-hexahydrobenzoxazole (2) is formed. Compound 2 and arylhydrazine-hydrochloride yield 1-carbamoyl-2-arylazocyclohex-1-ene (4a, b). In morpholine azocompounds 4a, b rearrange to hydrazones 5a, b. Compound 2 and hydrazine yield 4-(2-carbamoyl-cyclohexyl)-semicarbazide (10), 10 forms perhydroquinazoline-2,4-dione (11) by oxidation with iodine. 2 and cyanic acid yield the urea derivative 12. 2 and arylamine-hydrochloride afford the 2-arylamino-3a-hydroxy-7a-carbamoyl-hexahydrobenzoxazoles 13a, b. By fragmentation and “Dimroth-rearrangement” of 2 tetrahydrobenzoimidazolone, (14) is formed, 12 gives 1-carbamoyl-tetrahydrobenzoimidazolone (15). 2 and m-nitrobenzaldehyde yield “Schiff-base” 16. 2 and hydroxylamine sulphate form 2′-amino-2-hydroximino-cyclohexane-spiro-5′-oxazolin-4′-one (18) 18 and phenylhydrazine hydrochloride yield 1-phenylazo-2-ureido-carboxy-cyclohex-1-ene (19).
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19873290202
Permalink
