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The isolation, structural elucidation, directed preparation and some derivatives of three previously unknown heterocycles is reported. Arising from a guanidine based thymine synthesis, these novel compounds exhibit substituted and fused pyrimidine structures repectively.

Wahrend die drei stellungsisomeren Aminobenzoesauremethylester 1 mit Formaldehyd und Blausaure zu den entsprechenden N-Cyanmethyl-Derivaten 2 reagieren, liefert die Umsetzung mit Chloracetonitril das Chinazolinon-Derivat 4 bzw. die Amidine 8. On the Reaction of Aminobenzoates with Chloroacetonitrile Reactions of the isomeric methyl aminobenzoates 1 with formaldehyde and hydrocyanic acid yield the corresponding N-cyanomethyl derivatives 2. On the other hand, the quinazolinone 4 or the amidines 8 are formed by reaction of 1 with chloroacetonitrile.

2-Sulfinylbenzamide 3 reagieren mit Stickstoffwasserstoffsaure zu 3-Imino-3H-1λ4,2-benzisothiazol-1-oxiden 4, die durch Substitution am Imin-Stickstoff die Derivate 9–12 liefern. Cyclic Sulfoximides, IV. 3-Imino-3H-1λ4,2-benzisothiazole 1-Oxides 2-Sulfinylbenzamides 3 react with hydrazoic acid to yield 3-imino-3H-1λ4,2-benzisothiazole 1-oxides 4. The derivatives 9–12 are obtained by substitution at the imino-nitrogen.

Durch Ringschlus von 2-Hydroxybenzimidsaure-Derivaten 1 und 2 mit Carbonyl-Reagenzien werden 2H-1,3-Benzoxazin-2-one 3 und 4 erhalten. Heterocyclische o-Hydroxycarboximidsaure-Derivate 5 bzw. N,N′-uberbruckte Amidine 7 liefern die mehrkernigen Analoga 6 bzw. 8. Fused 2H-1,3-Oxazin-2-ones and -thiones Cyclisation of 2-hydroxybenzimidic acid derivatives 1 and 2 by carbonyl reagents yields 2H-1,3-benzoxazin-2-ones 3 and 4. Multinucleous compounds 6 resp. 8 are formed starting with heterocyclic o-hydroxycarboximidic acid derivatives 5 resp. N,N′-bridged amidines 7.

S-(2-Aminophenyl)sulfoximide 1 wurden nach verschiedenen Methoden in die 3-Amino-1λ4,2,4-benzothiadiazin-1-oxide 2, 4 und 6 ubergefuhrt. Umsetzung von 3-Methylthio-1λ4,2,4-benzothiadiazin-1-oxiden 8 mit Formylhydrazin lieferte die neuartigen tricyclischen Sulfoximide 9. Cyclic Sulfoximides, V. 3-Amino-1λ4,2,4-benzothiadiazine 1-Oxides The 3-amino-1λ4,2,4-benzothiadiazine 1-oxides 2, 4, and 6 were prepared from S-(2-aminophenyl)-sulfoximides 1 by various methods. The 3-methylthio-1λ4,2,4-benzothiadiazine 1-oxides 8 reacted with formylhydrazine to yield the novel tricyclic sufoximides 9.