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  • 1980-1984  (13)
  • 1960-1964  (4)
  • 1900-1904
  • 1800-1809
  • Heterocycles
  • 1
    ISSN: 1434-4475
    Keywords: Cinnamonitriles ; Cyanoethylations ; Heterocycles
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung 3-Antipyrinyl-5-aminopyrazol (1) reagierte mit Acrylnitril zu 5-Amino-1-β-cyanoethyl-3-antipyrinylpyrazol (2).2 konnte ebenfalls aus der Reaktion von β-Cyanethylhydrazin (3) und Verbindung4 erhalten werden.2 wurde mittels Essigsäure-Salzsäure glatt zu 2-Antipyrinyl-4,5,6,7-tetrahydropyrazolo[1,5-a]-pyrimidin-5-on (5) cyclisiert.5 konnte auch aus der Reaktion von1 mit Methylacrylat erhalten werden. Die Reaktion von1 mit Zimtsäurenitrilderivaten7 a–e ergab die Pyrazolo[1,5-a]pyrimidin-Derivate9,11 und12.
    Notes: Abstract 3-Antipyrinyl-5-aminopyrazole (1) reacted with acrylonitrile to afford 5-amino-1-β-cyanoethyl-3-antipyrinylpyrazole (2). Compound2 could also be obtained from the reaction of β-cyanoethylhydrazine (3) and compound4.2 was readily cyclized into 2-antipyrinyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidin-5-one (5) by acetic-hydrochloric acid.5 could be also obtained from the reaction of1 and methyl acrylate. The reaction of1 and cinnamonitrile derivatives7 a–e resulted in the formation of pyrazolo[1,5-a]pyrimidine derivatives9,11 and12.
    Type of Medium: Electronic Resource
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  • 2
    Electronic Resource
    Electronic Resource
    Springer
    Monatshefte für Chemie 115 (1984), S. 757-763 
    ISSN: 1434-4475
    Keywords: Heterocycles ; Synthesis
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung Die 5-Alkyl-5,6-dihydrobenzimidazo[2,1 -h]pteridin-2,4(1H,3H)-dione4 a-d wurden mittels Kondensation von 2-(Alkylaminomethyl)benzimidazolidhydrochloriden1 a–d mit 5-Brombarbitursäure (2) dargestellt. In ähnlicher Weise wurden die 5-Alkyl-5,6-dihydro-4a-nitrobenzimidazo[2,1 -h]pteridin-2,4(3H,4aH)-dione10 a–d über die Kondensation von1 a–d mit 5-Brom-5-nitrobarbitursäure (8) und nachfolgender Cyclisierung der intermediären 5-[(Benzimidazol-2-ylmethyl)alkylamino]-5-nitrobarbitursäuren9 a–d mit 5% NaOH dargestellt. Die thermische Cyclisierung der Produkte9 a–d wurde ebenfalls untersucht. Die Verbindungen wurden mittels Elementaranalyse, IR und PMR charakterisiert.
    Notes: Abstract 5-Alkyl-5,6-dihydrobenzimidazo[2,1 -h]pteridine-2,4(1H,3H)-diones (4 a–d) have been synthesised by the condensation of 2-(alkyl-aminomethyl)benzimidazole dihydrochloride (1 a–d) with 5-bromobarbituric acid (2). Similarly, 5-alkyl-5,6-dihydro-4 a-nitrobenzimidazo[2,1 -h] pteridine-2,4(3H,4aH)-diones (10 a–d) have also been synthesised by the condensation of1 a–d with 5-bromo-5-nitrobarbituric acid (8) followed by cyclisation of the intermediate 5-[(benzimidazol-2-ylmethyl)alkylamino]-5-nitrobarbituric acid (9 a–d) with 5% NaOH. Thermal cyclisation of the intermediates9 a–d have also been studied. Methylation of the compound10 a has been carried out with CH3I and K2CO3 usingD M F as solvent to confirm cyclisation. The structures are supported by elemental analyses, IR and PMR spectra.
    Type of Medium: Electronic Resource
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  • 3
    Electronic Resource
    Electronic Resource
    Springer
    Monatshefte für Chemie 114 (1983), S. 219-225 
    ISSN: 1434-4475
    Keywords: Cyanine dyes ; Dipyrazolylmethanes ; Heterocycles ; N-15-NMR ; O-17-NMR ; Phenazon
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract The 4-pyrazoline-3-one1 reacts with 4-dimethylaminobenzaldehyde to yield the stable asymmetric cyanine dye2b which reacts with1 to give the colorless (aryl) (dipyrazolyl) methane3b. Using aldehydes with less cationstabilizing groups the polymethines2 are not isolated but only the methanes3. The structures of2b and3 are discussed by1 H,13C and Hetero NMR spectra.
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  • 4
    Electronic Resource
    Electronic Resource
    Springer
    Monatshefte für Chemie 114 (1983), S. 339-342 
    ISSN: 1434-4475
    Keywords: Heterocycles ; Infrared ; 1H-NMR
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung 3-Methyl-6H-[1,2,4]triazolo[4′ ,3′ : 4,5] [1,3,4]thiadiazolo[2,3-b]chinazolin-6-on (6) wurde mittels Kondensation von Isatoesäureanhydrid (1) mit 4-Amino-5-mercapto-3-methyl[1,2,4]triazol (2) und anschließender Cyclisierung von Zwischenverbindung3 mit POCl3 und PCl3 dargestellt. Als Alternative konnte6 auch über die Kondensation von 3-Amino-2-mercapto-3H-chinazolin-4-on (7) mitN-Carbethoxyhydrazin in Gegenwart von HCl und anschließender Cyclisierung der Zwischenverbindung8 mit Essigsäure synthetisiert werden. Die Strukturen der Verbindungen wurden mittels IR,1H-NMR und Mikroanalyse nachgewiesen.
    Notes: Abstract 3-Methyl-6H-[1,2,4]triazolo[4′,3′: 4,5] [1,3,4]thiadiazolo[2,3-b]quinazolin-6-one (6) has been synthesized by the condensation of isatoic anhydride (1) with 4-amino-5-mercapto-3-methyl-[1,2,4]triazole (2) and final cyclisation of the intermediate3 with POCl3 and PCl3. Alternatively6 could also be synthesized by the condensation of 3-amino-2-mercapto-3H-quinazolin-4-one (7) withN-carbethoxy hydrazine in presence of hydrochloric acid and final cyclisation of the intermediate8 with acetic acid. The structures have been confirmed on the basis of IR, PMR and analytical results.
    Type of Medium: Electronic Resource
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  • 5
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 22 (1983), S. 171-190 
    ISSN: 0570-0833
    Keywords: 1,4-Diazines ; Pyrazine ; Heterocycles ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: In chemical research attention is increasingly being focussed on composite “complex” systems with special properties and functions. As components of such systems 1,4-diazines are steadily gaining in popularity. Here, 1,4-diazines means pyrazine and its derivatives as well as compounds with partial pyrazine structure; examples are quinoxaline, phenazine, pteridine, flavin and their derivatives. All these compounds are characterized by a low lying unoccupied π-molecular orbital and by the ability to act as bridging ligand. Due to these two properties 1,4-diazines, and especially their parent compound pyrazine, possess a characteristic reactivity. 1,4-Diazines may be employed to study inter- and intramolecular electron transfer in organic, inorganic and biochemical reactions. In the redox system of 1,4-diazines the paramagnetic 7π-electron intermediate exhibits exceptional stability, whereas the 1,4-dihydro-1,4-diazines with 8π-electrons in a six-membered ring are not generally accessible due to their potential antiaromaticity and their large excess of π electrons. Its inherent bifunctionality and the low lying unoccupied molecular orbital permit pyrazine to form coordination polymers having unusual electrical and magnetic properties. Finally, the phenomena observed for pyrazines may be used in the interpretation of the reactivity of naturally occurring 1,4-diazines, such as flavins and bioluminescent natural products.
    Additional Material: 6 Ill.
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  • 6
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 22 (1983), S. 337-350 
    ISSN: 0570-0833
    Keywords: Cyclization ; Chloroamines ; Alkenylamines ; Synthetic methods ; Heterocycles ; Free radicals ; Natural products ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Many N-chloroalkylamines with double bond(s) dissociate homolytically to give chlorine atoms and aminyl radicals which undergo intramolecular cyclization reactions. Here, the nature of the aminyl radicals (neutral, protonated, or complexed to metal salts) appears to be important. The reactivity varies strongly from one species to another, and their selectivities can be different towards addition, substitution, abstraction, or dimerization reactions. A good synthetic tool appears to be the “complexed radical”, which is generated under mild conditions. A variety of β-functionalized, substituted, fused, or bridged azaheterocycles with alkaloid part structures thus become easily accessible in high yields, in a regio- and, possibly, stereoselective manner. Many examples are discussed illustrating the synthetic possibilities, limitations, and mechanistic features of this cyclization process.
    Additional Material: 7 Tab.
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  • 7
    Electronic Resource
    Electronic Resource
    Springer
    Monatshefte für Chemie 113 (1982), S. 1283-1297 
    ISSN: 1434-4475
    Keywords: Heterocycles ; Keto-enol-tautomerism ; Synthesis ; 2H-Thiopyrane-2-ones and -2-thiones, 4-alkylamino and 4-alkoxy
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract The tautomers 4-hydroxy-6,6-dimethyl-5,6-dihydro-2H-thiopyran-2-thione (4 a) and 2-mercapto-6,6-dimethyl-5,6-dihydro-4H-thiopyran-4-one (4 b) resp. were synthesized by hydrolysis of 4-amino-5,6-dihydro-2H-thiopyranthiones6,8. On methylation of4 a,b only the S-methyl product7 is formed. Hydrolysis of 4-amino-2-methylthiothiopyranyliden iodides11 leads—depending on the amino group of11—either to the thiopyranone7 or to the 4-imino-thiopyranes12 and to β-amino-α,β,γ,δ-unsaturated-methyldithio carboxylates13. On reaction of4 a,b with hydrogenperoxyd the tautomers 4-hydroxy-5,6-dihydro-2H-thiopyran-2-one5 a and 5,6-dihydro-2H-thiopyran-2,4(3H)diones5 b resp. are formed.4 a,b and5 a,b undergo an aminolysis with prim. and sec. amines to the corresponding 4-amino-2H-thiopyran-2-thiones6,8 and -ones10 resp. On heating in alcohols the 4-alkoxy-thiopyrane-2-thiones and -ones9,14 are formed from4 a,b and5 a,b resp.
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  • 8
    Electronic Resource
    Electronic Resource
    Springer
    Monatshefte für Chemie 113 (1982), S. 1145-1150 
    ISSN: 1434-4475
    Keywords: Heterocycles ; Synthesis
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung Zur Synthese von 4H,6H-[1,3,4]thiadiazino[2,3-b]chinazolin-6-on (6a) wurde die Kondensation von 3-Amino-2-mercapto-3H-chinazolin-4-on (1) mit Allylbromid mit nachfolgender Behandlung mit Brom und Dehydrohalogenierung des bromierten Produktes4 mit ethanolischer Natronlauge herangezogen. Das zu6a isomere 2H,6H-Produkt6b wurde ebenfalls durch Kondensation von1 mit Bromaceton und nachfolgender Cyclisierung der Zwischenprodukte8 bzw.9 mit HBr oder H2SO4 erhalten. Die Strukturen wurden mittels IR und NMR abgesichert.
    Notes: Abstract 4H,6H-[1,3,4]Thiadiazino[2,3-b]quinazolin-6-one with a methyl group in position 3 (6a) has been synthesised by the condensation of 3-amino-2-mercapto-3H-quinazolin-4-one (1) with allyl bromide (2) followed by treatment with bromine and subsequent dehydrohalogenation of the brominated product (4) with ethanolic sodium hydroxide. Its isomeric 3-methyl-2H,6H-[1,3,4]thiadiazino[2,3-b]quinazolin-6-one (6b) has also been obtained by condensation of1 and bromoacetone (7) followed by cyclisation of the intermediates (8 or9) with hydrobromic acid or with concentrated sulphuric acid. The structures have been established on the basis of IR and PMR data.
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  • 9
    Electronic Resource
    Electronic Resource
    Springer
    Monatshefte für Chemie 112 (1981), S. 1187-1194 
    ISSN: 1434-4475
    Keywords: Heterocycles ; Knoevenagel reaction
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung Die Reaktion von Malodinitril mit Benzoylacetaniliden wurde untersucht. Die Struktur der dabei erhaltenen Verbindungen (2–4) wurde auf Basis der chemischen und spektroskopischen Eigenschaften zugeordnet.
    Notes: Abstract The reaction of benzoylacetanilides with malononitrile has been investigated. The structure of the compounds obtained (2, 3, 4) have been assigned on the basis of chemical properties and spectral data.
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  • 10
    Electronic Resource
    Electronic Resource
    Springer
    Monatshefte für Chemie 112 (1981), S. 1083-1090 
    ISSN: 1434-4475
    Keywords: Heterocycles ; 1 H-NMR ; Stereochemistry ; Synthesis
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung Es wurde eine Reihe von 5,12a-Dihydro-6-alkyl/aryl-6H-benzothiazolo [3,2-c]-1,3-dioxolo[4,5-g]chinazoline, sowohl mitcis-als auchtrans-ständigen Wasserstoffatomen an Kohlenstoff 6 und 12a, synthetisiert. Ebenso wurden auch Verbindungen dieses Systems mit Thiazol an Position 6 hergestellt. Die Strukturen wurden mittels IR- und NMR-spektroskopischen Daten abgesichert.
    Notes: Abstract Some 5,12a-dihydro-6-alkyl/aryl-6H-benzothiazolo[3,2-c]-1,3-dioxolo [4,5-g]quinazolines withcis as well astrans stereochemistry of the hydrogens at carbon 6 and 12a have been synthesised. The synthesis of another series of compounds of the above system with thiazole ring at position 6 has also been accomplished. The structures have been established on the basis of IR and PMR data.
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  • 11
    ISSN: 0570-0833
    Keywords: Hetero-1,3,5-hexatrienes ; Pericyclic reactions ; Photochemistry ; Cyclization ; Heterocycles ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Heterosubstituted 1,3,5-hexatrienes undergo thermal and photochemical cyclizations, most of which can be viewed as pericyclic reactions. Numerous cyclizations of this type have been reported in the literature. This article presents a systematic account of such reactions, classified according to the number and nature of the heteroatoms.
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  • 12
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 19 (1980), S. 947-973 
    ISSN: 0570-0833
    Keywords: Electrocyclic reactions ; Cyclization ; Heterocycles ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The principle of orbital control of pericyclic reactions has deepened our understanding of reaction phenomena and provided an excellent classification of these one-step processes. The electrocyclic reaction of the pentadienyl anion ⇌ cyclopentenyl anion type is relatively unimportant in all-carbon systems and has not even been verified in the case of the parent compound. In the heterocyclic series, however, where up to five C-atoms of the pentadienyl anion are replaced by heteroatoms, a multitude of ring closures and ring openings find their ordering principle in the mentioned electrocyclic reaction. The replacement of the carbon atoms by heteroatoms can take place isoinically, i. e., with retention of the anionic character, or isoelectronically. An isoelectronic replacement of CR2 in position 1 by NR2 OR, and or CR in position 3 by NR or O leads to a charge-free resonance structure for the open-chain species; the migration of the charge during the electrocyclization results in a correlation with a cyclic zwitterion. Conversely, isoelectronic exchange of CR in position 2 by NR or O produces a conjugated 1,3-dipole, which cyclizes to a charge-free unsaturated five-membered ring. Twofold isoelectronic exchange allows the whole process to take place in a cation. Selected examples are to shed light on the classification and the thermodynamics of this electrocyclic reaction.
    Additional Material: 2 Ill.
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  • 13
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 19 (1980), S. 276-289 
    ISSN: 0570-0833
    Keywords: Methylenecyclopropanes ; Heterocycles ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Heterocyclic three-membered rings with an exocyclic double bond merit special interest in view of their ring strain and their fascinating chemistry. Their synthesis, thermal decomposition, ring opening, and cycloaddition reactions will be discussed in this review. α-Lactams, alkylideneaziridines, diaziridinones, and diaziridinimines belong to the best known classes, but the chemistry of alkylideneoxiranes and -thiiranes, α-lactones, α-thiolactones, thiiranimines, and aziridinimines has also been studied to some extent. Two elusive three-membered rings are oxiranimines and thiaziridinimines; the former were postulated as reactive intermediates in the thermal decomposition of α-lactams, whereas the latter were trapped efficiently with double and triple bonds during thermolysis of N-sulfonyliminothiatriazolines. In spite of many attempts to prepare thione derivatives of the title compounds, they are still unknown. Included in this review are also some open-chain dipolar species which are isomeric with the heterocyclic three-membered rings.
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  • 14
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 3 (1964), S. 333-341 
    ISSN: 0570-0833
    Keywords: Strained molecules ; Heterocycles ; Diaziridines ; Diazirines ; Oxaziranes ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Since their discovery five years ago, the diaziridines have become an extensive and easily accessible class of compounds. Hydrolysis of these compounds effects a simple synthesis of hydrazine, alkylhydrazines, and N,N′-dialkylhydrazines. They are also powerful oxidizing agents. The rigidity of the three-membered ring gives rise to a few stereoelectronic peculiarities. Investigations on the mechanism of formation of the three-membered rings led to a new synthesis of oxaziranes and to discovery of the isomeric oximes with a three-membered ring structure. The latter decompose readily to form diimide. Diazirines are cyclic isomers of the aliphatic diazo compounds and are surprisingly easy to obtain by dehydrogenation of suitable diaziridines; they are chemically much more stable than the linear isomers. Grignard reagents add onto the N=N double bond without destruction of the three-membered ring. Thermal decomposition yields carbenes.
    Additional Material: 1 Ill.
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  • 15
    ISSN: 0570-0833
    Keywords: Kinetics ; Dipolar cycloaddition ; Cycloaddition ; Heterocycles ; Reaction mechanisms ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Criteria for the mechanism of 1,3-dipolar cycloadditions which lead to 5-membered rings are provided by the stereoselectivity observed with cis-trans isomeric dipolarophiles, by the effect of solvent and substituents on the rate constants, by the activation parameters, and by orientation phenomena. A concerted addition, which can also be described in terms of molecular orbitals and in which the two new σ-bonds are formed simultaneously, although not necessarily at equal rates, offers the best explanation of the experimental facts.
    Additional Material: 2 Ill.
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  • 16
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 2 (1963), S. 459-476 
    ISSN: 0570-0833
    Keywords: Aminoguanidine ; Heterocycles ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Due to its unique structure, aminoguanidine is capable of reacting as a derivative of hydrazine, guanidine or formamidine. Addition and condensation reactions yield products which can be cyclized to heterocyclic compounds. Frequently, heterocyclics are directly accessible from aminoguanidine in one stage.
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  • 17
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 2 (1963), S. 565-598 
    ISSN: 0570-0833
    Keywords: Dipolar cycloaddition ; Cycloaddition ; Heterocycles ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: In contrast to the very large number of special methods applicable to syntheses in the heterocyclic series, relatively few general methods are available. The 1,3-dipolar addition offers a remarkably wide range of utility in the synthesis of five-membered heterocycles. Here the “1,3-dipole”, which can only be represented by zwitterionic octet resonance structures, combines in a cycloaddition with a multiple bond system - the “dipolarophile” - to form an uncharged five-membered ring. Although numerous individual examples of this reaction were known, some even back in the nineteenth century, fruitful development of this synthetic principle has been achieved only in recent years.
    Additional Material: 4 Tab.
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