Regular Issue

Vol. 9, No. 3, 1978

10 data found. 1 - 10 listed
Communication | Regular issue | Vol 9, No. 3, 1978, pp. 243 - 246
Published online:
DOI: 10.3987/R-1978-03-0243
Triazolines X. Organic Synthesis via 1,2,3-Triazoline Intermediates. A Unique Synthesis of 4-Anilinopyridazine

Panlaja K. Kadaba* and John Triplett

*College of Pharmacy, University of Kentucky, Lexington, KY 40536-0053, U.S.A.


The paper illustrates the utility of the 1,2,3-triazoline heterocycle in organic synthesis. The 4,5-acyl-substituted triazoline (2) decomposes in situ to yield the enaminodiketone (3) and the diacylaziridine (5). With hydrazine, (3) undergoes ring closure to yield the hitherto unknown 4-anilinopyridazine (4); (5), however, yields the pyrazole (7). A mechanism is suggested for the formation of (7).

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Communication | Regular issue | Vol 9, No. 3, 1978, pp. 247 - 255
Published online:
DOI: 10.3987/R-1978-03-0247
Benzopyrano[3,4-b]indoles and Quinolines

Giovanni Alunni Bistochi,* Giovanni De Meo, Adolfo Ricci, Alain Croisy,* and Pierre Jacquignon

*Institut de Chimie des Substtances Naturelles, C. N. R. S., 91190 Gif-sur-Yvette, France


Various benzopyranoindoles and benzopyranoquinolines derived from chroman-3-one have been synthesized with the aim of including them in structure activity studies of the carcinogenic potency in the carbazole and acridine series. From a physicochemical point of view, the structure of the isolated compounds is discussed in regard to some of their NMR properties.

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Communication | Regular issue | Vol 9, No. 3, 1978, pp. 257 - 261
Published online:
DOI: 10.3987/R-1978-03-0257
Hispanolone, a New Furanoditerpene

Giuseppe Savona, Franco Piozzi,* and Benjamin Rodriguez

*Dipartimento di Chimica Organica, Università digli Studi di Palermo, Via Archirafi 20 90123 Palermo, Italy


Hispanolone, a new furanoditerpene occurring in Ballota hispanica (Labiatae), is attributed the structure [I] with normal labdane skeleton.

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Communication | Regular issue | Vol 9, No. 3, 1978, pp. 263 - 266
Published online:
DOI: 10.3987/R-1978-03-0263
Syntehsis and Conformational Analysis of Tetrahydro-1,2,5-oxadiazines

Alan A. Katritzky* and Ranjan Patel

*School of Chemical Sciences, University of East Anglia, Norwich, Northfolk NR4 7TJ, U.K.


Tetrahydro-1,2,5-oxadiazines are prepared for the first time. They show two coalescence processes in the n. m. r. spectra, corresponding to (a) ring reversal or 2-NMe inversion and (b) 5-NMe inversion.

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Communication | Regular issue | Vol 9, No. 3, 1978, pp. 267 - 270
Published online:
DOI: 10.3987/R-1978-03-0267
The Synthesis and Comformational Analysis of Tetrahydro-1,2,4- and 1,2,5-oxadiazines

Frank G. Riddell* and Eric S. Turner

*School of Chemistry, The University, Hull HU6 7RX, U.K.


Derivatives of tetrahydro-1,2,4-oxadiazine and tetrahydro-1,2,5-oxadiazine have been prepared. Both systems show coalescences in their nmr spectra corresponding to either ring inversion or 2-N-methyl inversion.

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Communication | Regular issue | Vol 9, No. 3, 1978, pp. 271 - 274
Published online:
DOI: 10.3987/R-1978-03-0271
Coupling Reaction of Monosubstituted Acetylenes with Iodopyrimidines

Kiyoto Edo, Hiroshi Yamanaka,* and Takao Sakamoto

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan


The pyrimidine derivatives containing an acetylenic side chain at the 2- or 4-position were synthesized by means of the reaction of alkyl(or phenyl)acetylenes with 2-iodo- or 4-iodopyrimidines in the presence of a palladium triphenylphosphine complex in yields ranging from 70 to 95 %. The reaction readily proceeded in both 2,4-diiodo- and 4,6-diiodopyrimidines to give the corresponding dialkynyl derivatives.

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Communication | Regular issue | Vol 9, No. 3, 1978, pp. 275 - 279
Published online:
DOI: 10.3987/R-1978-03-0275
Reaction of 4-Azido-5-(1-cyanoethylidine)-1,3-dimethyl-2-pyrrolinone with Amines. A Convenient Synthesis of 3-Aminomethyl-4-amino-5-(1-cyanoethylidine)-1-methyl-2-pyrrolinones

Annlie Sing and Harold W. Moore*

*Department of Chemistry, University of California, One Shields Avenue, Davis, CA 95616-5295, U.S.A.


The reaction of 4-azido-5-(1-cyanoethy1idine)-1,3-dimethyl-2-pyrrolinone with amines (piperidine, morpholine, pyrrolidine, and aniline) is described. This reaction results in the incorporation of an aminomethyl group at position -3 with concomitant reduction of the azide group to a primary amine, i. e., the formation of 3-aminomethyl-4-amino-5-(1-cyanoethylidine)-2-pyrrolinones, 6a-d.

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Report | Regular issue | Vol 9, No. 3, 1978, pp. 281 - 286
Published online:
DOI: 10.3987/R-1978-03-0281
Mechanistic Aspects of Photochemistry of Ethl 2-Cyano-1,2-dihydroquinoline-1-carboxylates (Reissert Compounds)

Masazumi Ikeda,* Saeko Matsugashita, and Yasumitsu Tamura

*Faculty of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Toyonaka, Osaka 560-0043, Japan


The previously proposed azahexatrienes are shown not to be intermediates of the photochemical transformation of ethyl 2-cyano-1,2-dihydroquinoline-1-carboxylates to cycloprop[b]indoles, allenic compounds and/or ethanol adducts.

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Report | Regular issue | Vol 9, No. 3, 1978, pp. 287 - 291
Published online:
DOI: 10.3987/R-1978-03-0287

Fuk L. Lam and James C. Parham*

*Laboratory for Bioorganic Chemistry, Memorial Sloan-Kettering Cancer Center, 1275 York Avenue, New York NY 10021, U.S.A.


The previously unreported 6,7-dimethylpurine was obtained in low yield by methylation of the anion of 6-methylpurine.

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Review | Regular issue | Vol 9, No. 3, 1978, pp. 293 - 351
Published online:
DOI: 10.3987/R-1978-03-0293
Synthesis of Pyrrolo[1,2-a]indoles and Related Systems

Tetsuji Kametani* and Kimio Takahashi

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan


The various syntheses of pyrrolo[1,2-a]indoles and related compounds, which are the main framework of the mitomycins, are described.

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10 data found. 1 - 10 listed