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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.

Monodeoxy-1,4:3,6-dianhydrohexitol nitrates with (5) or without (6) an additional chloro substituent were synthesized, starting from 1,4:3,6-dianhydrohexitol-monoacetates, via 3 as key intermediates. Attempts to generate an unsaturated nitrate ester resulted in a DBN alkylation product (9). Both the endo- and exo-configurated monodeoxy-1,4:3,6-dianhydrohexitol nitrates have been prepared. Attempts to generate an unsaturated nitrate ester resulted in a DBN alkylation produkt.

Publisher Summary This chapter provides an overview of 1,4:3,6-dianhydrohexitol compounds. In 1884, 1,4:3,6-dianhydro- D -mannitol was described as the first member of the 1,4:3,6-dianhydrohexitols series. The 1,4:3,6-dianhydrohexitols belong to the so-called “biomass-derived substances” obtainable from natural products, and are thus classified as “regenerable resources.” Because of the lack of a chromophoric group, normal isohexides do not exhibit characteristic absorption bands in the ultraviolet region. Except for chromophoric substituents, only for the monoketones having the carbonyl group in the 2-position and the diketone( both derived from isosorbide), an absorption band is observed at 267 nm (in water). Isohexide mononitrates, as well as dinitrates, show a weak, positive dichroic band at 265 nm and a second, stronger one near 228 nm, which is positive for endo-R-nitrato and negative for em-S-nitrato groups. For isosorbide dinitrate, both dichroic bands are positive. This chapter provides details on the nomenclature of bridged systems and fused systems. It also discusses spectroscopic properties, structural aspects, and analytical detection concepts of isohexides and explains the preparation of the parent compounds.

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.

Novel types of nucleoside analogues, being potential anticancer and antiviral candidates and exhibiting a 1,4:3,6-dianhydrohexitol moiety as the carbohydrate part of the molecule, are described. The synthesis has been performed by reacting the appropriate chloromethylated, protected dianhydrohexitol with silylated bases.

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.