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1

Digitale Medien

The Synthesis of [4-Carboranylalanine, 5-Leucine]-Enkephalin (Including an Improved Preparation of t-Butoxycarbonyl-L-o-carboranylalnine, New Derivatives of L-Propargylglycine, and a Note on Melanotropic and Opiate Receptor Binding Characteristics)This work was supported by research grants of the Swiss National Science Foundation and the Swiss Federal Institute of Technology. Abbreviations are according to the IUPAC-IUB Commission on Biochemical Nomenclature [1] and Houben-Weyl [2]: Car represents L-propargylglycine is and Pra L-propargylglycine. A former statement in the summary of [3] that L-propargylglycine is a new amino acid is incorrect; only its derivatives with protecting groups suitable for peptide synthesis were new. The free amino acid had been described earlier as the racemate [4] and as the individual enantiomers [5]. (1979)

Fauchère, Jean-Luc ; Leukart, Othmar ; Eberle, Alex ; [weitere]

New York, NY : Wiley-Blackwell

Helvetica Chimica Acta 62 (1979), S. 1385-1395

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ISSN: 0018-019X

Schlagwort(e): Chemistry ; Organic Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: The title compound, an analogue of [Leu5]-enkephalin with L-o-carboranylalanine replacing L-phenylalanine in position 4, was prepared by fragment condensation. The analogue has a 3-fold higher affinity for rat brain opiate receptors in the [3H]naloxone competition assay than natural [Leu5]-enkephalin. Like [Leu5]-enkephalin and Na-acetyl-[Leu5]-enkephalin, the N-terminal tripeptide fragment, H · Tyr-Gly-Gly · OH, had no melanotropic activity in the Rana pipiens frog skin assay.A convenient, direct synthesis of methyl t-butoxycarbonyl-L-propargylglycinate is described, and the 13C-NMR. spectra of L-o-carboranylalanine recorded. The procedure was extended to the preparation of BOC · Car-Leu · OMe from BOC · Pra-Leu · OMe. A number of new propargylglycine derivatives are reported.

Zusätzliches Material: 3 Ill.

Materialart: Digitale Medien

URL: http://dx.doi.org/10.1002/hlca.19790620502

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2

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Phenylselenoacetaldehyde, a Useful Reagent for the Homologative Conversion of Halides to Phenylselenomethyl KetonesDedicated to Professor Edgardo Giovannini on his 70th anniversary (1979)

Baudat, Roger ; Petrzilka, Martin

New York, NY : Wiley-Blackwell

Helvetica Chimica Acta 62 (1979), S. 1406-1410

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ISSN: 0018-019X

Schlagwort(e): Chemistry ; Organic Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: The conversion of primary, secondary and vinylic halides to the two C-atoms homologated phenylselenomethyl ketones 8 is described. The method involves addition of the readily available phenylselenoacetaldehyde 5 to the Grignard reagents 9 and oxidation of the resulting β-hydroxy-selenides 10 (Scheme 3).

Zusätzliches Material: 1 Tab.

Materialart: Digitale Medien

URL: http://dx.doi.org/10.1002/hlca.19790620505

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3

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Anil-Synthese. 20. Mitteilung19. Mitt. siehe [1].. Über die Herstellung von Stilbenyl-Derivaten des 1,2,4,-OxadiazolsHerrn Professor Dr. Dr. h.c. Edgardo Giovannini zum 70. Geburtstag gewidmet (1979)

Berger, Hanny ; Siegrist, Adolf Emil

New York, NY : Wiley-Blackwell

Helvetica Chimica Acta 62 (1979), S. 1411-1428

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ISSN: 0018-019X

Schlagwort(e): Chemistry ; Organic Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: Preparation of Stilbenyl Derivatives of 1,2,4-OxadiazolesSchiffs bases derived from 3- and 5-(p-formylphenyl)-phenyl-1,2,4-oxadiazoles and chloroanilines are reacted with various p-tolyl substituted aromatic heterocycles in the presence of dimethylformamide and potassium hydroxide to yield the corresponding heterocyclic substituted stilbenes (‘Anil synthesis’). The reactivity of 5-[4-(chlorophenylimino-methyl)phenyl]-3-phenyl-1,2,4-oxadiazoles is very low and side reactions will predominate.

Zusätzliches Material: 1 Ill.

Materialart: Digitale Medien

URL: http://dx.doi.org/10.1002/hlca.19790620506

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4

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(Perhalogenmethylthio)heterocyclen. XIX. Mitt.: s. [1].. Säurekatalysierte Substitutionen an (Perchlorfluormethylthio)pyrrolen und deren agrobiologische Wirkung (1979)

Dorn, Silvia ; Eggenberg, Peter ; Gerstenberger, Michael R. C. ; [weitere]

New York, NY : Wiley-Blackwell

Helvetica Chimica Acta 62 (1979), S. 1442-1450

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ISSN: 0018-019X

Schlagwort(e): Chemistry ; Organic Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: (Perhalomethylthio)heterocycles. XIX. Mitt.: s. [1]. . Acid-catalyzed substitutions on (perchlorofluoromethylthio)pyrroles and their agro-biological activitiesIn the presence of C4F9SO3H the (perhalomethylthio)pyrroles 1a-c react with Cl3-nFnCSCl (n = 1-3) to give mixtures of the 2,5- and 2,4-disubstituted pyrroles 2a-f and 3a-h. 2a and 3a react with CF3SCl (catalyst CF3SO3H) yielding 2,3,5-tris (trifloromethylthio)pyrrole (4a), which under similar conditions reacts further to give 2,3,4,5-tetrakis (trifluoromethylthio)pyrrole (5). As a by-product during the conversion of 3a to 4a 2,3,4-tris (trifluoromethylthio)pyrrole (4b) is formed. The pyrroles 2a, 4a and 5 form the mercury salts 6a-c; compound 5 yields also a silver salt 7. The 1H- and 19F-NMR. spectra are discussed and the agro-biological properties of the compounds investigated.

Zusätzliches Material: 4 Tab.

Materialart: Digitale Medien

URL: http://dx.doi.org/10.1002/hlca.19790620508

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5

Digitale Medien

Nouvelle méthode de préparation d'éthers vinyliques à partir d'acétals (1979)

Barbot, Francis ; Miginiac, Philippe

New York, NY : Wiley-Blackwell

Helvetica Chimica Acta 62 (1979), S. 1451-1457

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ISSN: 0018-019X

Schlagwort(e): Chemistry ; Organic Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: A new way to vinylic ethers from acetalsAcetals react at low temperatures in presence of a Lewis acid (aluminium chloride or magnesium bromide) with tertiary amine to give in good yields the vinylic ethers corresponding to the elimination of one molecule of alcohol.

Zusätzliches Material: 4 Tab.

Materialart: Digitale Medien

URL: http://dx.doi.org/10.1002/hlca.19790620509

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6

Digitale Medien

Additionsreaktionen von 3-Dimethylamino-2,2-dimethyl-2H-azirin an Phenylisocyanat und DiphenylketenHerrn Prof. Dr. Dr. h.c. Edgardo Giovannini zum 70. Geburtstag gewidmet (1979)

Mukherjee-Müller, Gabriele ; Heimgartner, Heinz ; Schmid, Hans

New York, NY : Wiley-Blackwell

Helvetica Chimica Acta 62 (1979), S. 1429-1441

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ISSN: 0018-019X

Schlagwort(e): Chemistry ; Organic Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: Addition Reaction of 3-Dimethylamino-2,2-dimethyl-2H-azirine with Phenylisocyanate and Diphenylketene3-Dimethylamino-2,2-dimethyl-2H-azirine (1a) reacts with carbon disulfide and isothiocyanates with splitting of the azirine N(1), C(3)-double bond to give dipolar, fivemembered heterocyclic 1:1 adducts. In some cases, these products can undergo secondary reactions to yield 1:2 and 1:3 adducts. In this paper it is shown that the reaction of 1a with phenylisocyanate also takes place by cleavage of the N(1), C(3)-bond, whereas with diphenylketene N(1), C(2)-splitting is observed.The reaction of 1a and phenylisocyanate in hexane at room temperature yields the 1:3 adduct 2 in addition to the trimeric isocyanate 3 (Scheme 1). A mechanism for the formation of 2 is given in Scheme 5. Hydrolysis experiments with the 1:3 adduct 2, yielding the hydantoins 4-6 and the ureas 7 and 8 (Schemes 3 and 5), show that the formation of this adduct via the intermediates d, e and f is a reversible reaction.The aminoazirines 1a and 1b undergo an addition reaction with diphenylketene to give the 3-oxazolines 14 (Scheme 8), the structure of which has been established by spectral data and oxidative degradation of 14a to the 3-oxazolin-2-one 15 (R1 — R2 — CH3, Scheme 9).

Materialart: Digitale Medien

URL: http://dx.doi.org/10.1002/hlca.19790620507

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7

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1H-NMR.-spektroskopische Analyse von prochiralen Allencarbonsäureestern mit optisch aktiven Europium-VerschiebungsreagenzienHerrn Prof. Dr. Dr. h. c. Edgardo Giovannini, in Verehrung zum 70. Geburtstag gewidmet (1979)

Lang, Robert W. ; Hansen, Hans-Jügen

New York, NY : Wiley-Blackwell

Helvetica Chimica Acta 62 (1979), S. 1458-1465

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ISSN: 0018-019X

Schlagwort(e): Chemistry ; Organic Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: 1H-NMR. Spectroscopic Analysis of Prochiral Allenic Esters Using Optically Active Europium Shift ReagentsThe prochiral allenic methyl esters 1-4 (cf. Scheme) show in the presence of 1 mol-equiv. tris[3-(heptafluorobutyryl)-(+)-camphorato]europium (III) (Eu (hfc)3) in 1,1,2-trichloro-1,2,2-trifluoroethane (TCFE) induced unlike 1H-NMR. shift differences (ΔΔδ) for the enantiotopic protons and methyl groups on C(4), respectively (cf. Fig. 2 and 3). This effect allows to determine directly the 2JH,H coupling constants of the geminal protons on C(4) of the allenic esters 1 (15.5 Hz) and 2 (14.5 Hz) (cf. Table 2).

Zusätzliches Material: 3 Ill.

Materialart: Digitale Medien

URL: http://dx.doi.org/10.1002/hlca.19790620510

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8

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Heterocyclisch anellierte Derivate des Strychnins: Imidazo-, Oxazolo- und (1,3-Dioxolo)strychnineHerrn Prof. Hellmut Bredereck zum 75. Geburtstag gewidmet (1979)

Edenhofer, Albrecht ; Arnold, Wolf

New York, NY : Wiley-Blackwell

Helvetica Chimica Acta 62 (1979), S. 1466-1474

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ISSN: 0018-019X

Schlagwort(e): Chemistry ; Organic Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: Heterocyclic anellated derivatives of strychnine: Imidazo-, oxazolo- and (1,3-dioxolo)strychnineThe synthesis of imidazo-, oxazolo- and dioxolo-strychnine derivatives, anellated at the 2,3-position of the aromatic nucleus is described. The spectroscopic properties of these compounds and of some intermediates are given.

Zusätzliches Material: 3 Tab.

Materialart: Digitale Medien

URL: http://dx.doi.org/10.1002/hlca.19790620511

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9

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Norrish Type I Cleavage of Aliphatic Carboxylic Acids and Esters in Solution. A CIDNP.-studyHerrn Prof. A.S. Dreiding zum 60. Geburtstag gewidmet (1979)

Kaiser, Tony ; Fischer, Hanns

New York, NY : Wiley-Blackwell

Helvetica Chimica Acta 62 (1979), S. 1475-1484

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ISSN: 0018-019X

Schlagwort(e): Chemistry ; Organic Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: UV.-irradiation of pivalic and isobutyric acid and their methyl esters as well as of α-hydroxy isobutyric and malonic acid in solution lead to chemically induced dynamic nuclear polarization (CIDNP.) of parent compounds and of various reaction products. CIDNP.-effects and product distributions confirm α-cleavage of the C(α), CO bond to be the major mode of photodecomposition. Scavenger experiments indicate that decomposition of the molecules from a triplet excited state is roughly equally or more probable than from a singlet excited state. Quantum yields of educt disappearance are also given for the methyl esters of pivalic and isobutyric acid.

Zusätzliches Material: 2 Ill.

Materialart: Digitale Medien

URL: http://dx.doi.org/10.1002/hlca.19790620512

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10

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Displacement of Activated Amino Groups. C,N- vs. N,S-Bond Cleavage in the Reaction of N-Alkyl-disulfonamides with NucleophilesDedicated to Professor Edgardo Giovannini on occasion of his 70th birthday (1979)

Müller, Paul ; Thi, Minh Phuong Nguyen

New York, NY : Wiley-Blackwell

Helvetica Chimica Acta 62 (1979), S. 1485-1492

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ISSN: 0018-019X

Schlagwort(e): Chemistry ; Organic Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: Sodiumthiophenoxide and sodiumphenylselenide react with N-benzyl- and N-hexyl-di-p-toluenesulfonamides (1 and 2) via displacement at the C-atom to afford the corresponding organosulfides and selenides in yields of 68-96%. In contrast, sodium cyanide converts disulfonamides to monosulfonamides by attack on the S-atom. The different selectivities of phenylsulfide and selenide as compared to cyanide anions with respect to attack on the C- and S-atoms are rationalized on the grounds of the HSAB (hard and soft acids and bases) principle of Pearson.

Zusätzliches Material: 3 Tab.

Materialart: Digitale Medien

URL: http://dx.doi.org/10.1002/hlca.19790620513

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