Spectroscopic Department, EGIS Pharmaceuticals, P. 0.8. 7 00, H-7 475 Budapest, Hungary ~~ endo-and exo-Norbornene (1) and (3) and norbornane (2) and (4) amino acids and isothiocyanates give methylene-bridged 2-thioxohexahydro-(10) and (1 1) and octahydro-(12) and (13)-quinazolin-4ones. Compounds (10) and (11) decompose in a retro-Diels-Alder reaction when heated to melting, to give new 3-substituted thiouracils (1 4a-e); no convenient general suitable method was previously known for the preparation of these compounds.Besides the theoretical, primarily stereochemical, interest in compounds with a norbornane skeleton, they are also used as pharrnace~ticals.~.~ We therefore previously prepared a number of 1,3-oxazine derivatives with norbornane and norbornene skeleton^.^ These compounds and their derivatives with a fused azetidinone ring were systematically studied through H and 13C n.m.r. ~pectroscopy.~In the present work we report on the synthesis of methylenebridged saturated and partially saturated thioxoquinazolones; the retrodiene reactions of these compounds occur under mild conditions and afford a very convenient route to new thiouracil derivatives, as shown in the Scheme.
Es wurden I-substituierte (5-Tetrazolyl)mesityldisulfide hergestellt, welche zu Disulfid-S2,Sz-dioxiden (Thiosulfonate) oxidiert wurden. Deren Struktur und die der friiher hergestellten 1 -substituierten (5-Tetrazolyl)p-tolyIdisulfid-S2,S2-dioxide wurde anhand ihrer IRund NMR-Spektren wahrscheinlich gemacht. Die angenommenen Strukturen wurden durch Synthese bewiesen.
Aromatic Sulfenyl Chlorides, M 1)
Prepration, Oxidntion, and Spectroscopic Investigation of 1-Substituted ITetrpzolyl Aryl Disulfides1 -Substituted 5-tetrazolyl mesityl disulfides were synthesized which on oxidation with hydrogen peroxide gave disulfide SZJz-dioxides (thiolsulfonates). The structure of these as well as that of the 1 -substituted 5-tetrazolyl ptolyl disulfide S2,Sklioxides synthesized earlier was elucidated by means of their i. r. and n. m. r. spectra. The supposed structures have been established by synthesis.
Umsetzung der Tetrazolthione (I) mit dem Sulfenylchlorid (II) liefert die Disulfide (III), von denen einige zu den Thiolsulfonaten (IV) oxidiert werden.
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