ISSN:
0075-4617
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
On the Joint Action of Elemental Sulfur and Gaseous Ammonia on Ketones, LXXIV1). -Hydrazinolysis of 3-Imidazoline-5-thiones to 1,2-Dihydro- and 1,2,3,4-Tetrahydro-S-tetrazines1,2-Dihydro-S-tetrazines 2 and 1,2,3,4-tetrahydroStetrazines 3 are synthesized by reacting 3-imidazoline-5-thiones 1 with hydrazine hydrate in ethanol. Compounds 3 are also obtained from α-oxothioamides 4 by condensation with ketones and hydrazine hydrate. With3 acetone gives the condensation products 5. - 3-Imidazoline-5-thiones lh, m, and o having bulky groups react with hydrazine hydrate to give the 4-hydrazino-2H-imidazoles 6. 3-Imidazolin-5-ones 7 are cleaved by hydrazine hydrate to α-hydrazonoamides 9; no reaction with 4-methylthio-2H-imidazoles 8 was observed.
Notes:
1,2-Dihydro-S-tetrazine 2 und 1,2,3,4-Tetrahydro-S-tetrazine 3 bilden sich durch Umsetzung von 3-Imidazolin-5-thionen 1 mit Hydrazin-hydrat in Äthanol. Die Verbindungen 3 erhält man auch durch Kondensation von α-Oxothioamiden 4 mit Ketonen und Hydrazin-hydrat. Mit Aceton reagiert 3 zu den Kondensationsprodukten 5. - 3-Imidazolin-5-,thione 1h, m und o mit sperrigen Substituenten setzen sich mit Hydrazin-hydrat zu 4-Hydrazino-2H-imidazolen 6 um. 3-Imidazolin-5-one 7 werden durch Hydrazin-hydrat zu α-Hydrazono-amiden 9 gespalten, während 4-Methylthio-2H-imidazole 8 nicht reagieren.
Additional Material:
3 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.197419740115
