HETEROCYCLES
An International Journal for Reviews and Communications in Heterocyclic ChemistryWeb Edition ISSN: 1881-0942
Published online by The Japan Institute of Heterocyclic Chemistry
Regular Issue
Vol. 9, No. 7, 1978
Published online:
■ The 1,3-Dipolar Cycloaddition Reaction of Fervenulin 4-Oxides with Dimethyl Acetylenedicarboxylate, a Novel Synthesis of Pyrrolo[3,2-d]pyrimidines (9-Deazapurines)
Keitaro Senga,* Misuzu Ichiba, and Sadao Nishigaki
*Pharmaceutical Institute, School of Medicine, Keio University, Shinanomachi 35, Shinjuku, Tokyo 160-0016, Japan
Abstract
The 1,3-dipolar cycloaddition reaction of fervenulin 4- oxides (6,8-dimethylpyrimido[5,4-e]-as-triazine-5,7(6H, 8H)-dione 4-oxides) with dimethyl acetylenedicarboxylate afforded the corresponding 7-carbomethoxy-l,3-dimethylpyrrolo[3,2-d]pyrimidine-2,4(1H,3H)-diones.
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■ Potassium Transport in Plant Leaves; Synthesis of Roseoside Tetraacetate
Kenneth L. Stuart* and Yvonne G. Whittle
*Department of Chemistry, Mona Campus, University of the West Indies, Mona, Kingston 7, Jamaica
Abstract
The plant hormones vomifoliol and abscisic acid appear to be involved in the transport of potassium in plant leaves. A novel transport mechanism is proposed. The first synthesis of roseoside tetraacetate is reported.
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■ A New Approach to Quinazolinocarboline Alkaloids: Synthesis of (±)-Evodiamine, Rutaecarpine and Dehydroevodiamine
Bruno Danieli* and Giovanni Palmisano
*Dipartimento di Chimica Organica e Industriale, Università degli Studi di Milano, Via Venzian 21, 20133 Milano, Italy
Abstract
Treatment of the tetracyclic lactam (I) with Hg(OAc)2 gives (±)-evodiamine (III) which is in turn regiospecifically oxidized to rutaecarpine (IVa) by MnO2 or to dehydroevodiamine (V) by other oxidants.
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■ Approaches to the Mitomycins: 4,4a-Secodeiminoquinones
Richard W. Franck,* Katsuji Miyano, and John F. Blount
*Department of Chemistry, Fordham University, Bronx, NY 10458, U.S.A.
Abstract
Frameworks containing all the stereochemical and functional features except the aziridine and the 4,4a C-N bond of both epimeric series of the mitomycins are prepared in a short synthesis.
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■ A Convenient Photosynthesis of Heterocyclic Quinones by a One-pot Reaction
Mitsuo Akiba,* Satoshi Ikuta, and Toyozo Takada
*School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan
Abstract
The photochemical reaction of 2-chloro-3-acetylethoxycarbonylmethyl-1,4-naphthoquinone (1b) with various secondary amines (pyrrolidine, piperidine, morpholine, and hexamethyleneimine) provided a convenient, one-pot, preparative route to the heterocyclic quinones (4b) as a mixture of stereoisomers due to the different substituents. A similar photoreaction of 2-chloro-3-ethoxycarbonylcyanomethyl-1,4-naphthoquinone (1c) with amines gave selectively one diastereomer of the series (4c).
The stereochemical studies on these photoproducts were investigated by using the europium-shifted spectra.
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■ A Simple Synthesis of 2-Substituted 4-Oxazolidinones and 1,3-Oxazin-4-ones from Amide-Aalcohols (Studies on the Syntheses of Heterocyclic Compounds 748)
Tetsuji Kametani,* Kazuo Kigasawa, Mineharu Hiiragi, Nagatoshi Wagatsuma, Toshitaka Kohagisawa, and Hitoshi Inoue
*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan
Abstract
Acid-catalyzed cyclisation of the secondary amides (7 - 10) possessing a hydroxyl group at α- or β-position with various carbonyl compounds gave the novel 2-substituted 4-oxazolidinones (11 - 15) and tetrahydro-1,3-oxazin-4-ones (16 - 24).
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■ A Simple Synthesis of 4-Thiazolidinones, Tetrahydro-1,3-thiazin-4-one and Hexahydro-1,3-thiazepin-4-ones from Amide-Thiols (Studies on the Syntheses of Heterocyclic Compounds 749)
Tetsuji Kametani,* Kazuo Kigasawa, Mineharu Hiiragi, Nagatoshi Wagatsuma, Toshitaka Kohagisawa, and Hitoshi Inoue
*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan
Abstract
Acid-catalyzed cyclisation reaction of the secondary amides (3 - 10) possessing a mercapto group at α-, β- or γ-position with aldehydes gave some novel 4-thiazolidinones (11 - 14), tetrahydro-1,3-thiazin-4-ones (15 - 21), and hexahydro-1,3-thiazepin-4-ones (22 and 23), and the reduction of the cyclisation products, 12, 16 and 23 with lithium aluminium hydride afforded thiazolidine (26), tetrahydro-1,3-thiazine (27), and hexahydro-1,3-thiazepine (28), respectively.
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■ Studies on Ketene and Its Derivatives (XC). Reaction of Diketene with Ethyl Cyanoacetate and Malononitrile
Tetsuzo Kato,* Yukio Kubota, Michiko Tanaka (née Ishikawa), Hitoshi Takahashi, and Takuo Chiba
*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan
Abstract
Reaction of diketene with ethyl cyanoacetate (7) gives ethyl 2-amino-6-methyl-4-pyrone-3-carboxylate (9), which is transformed to ethyl 4-hydroxy-6-methyl-2-pyridone-3-carboxylate (11). Similarly, diketene reacts with malononitrile (8) to give 2-amino-3-cyano-6-methyl-4-pyrone (10), which is converted to 3-cyano-4-hydroxy- 6-methyl-2-pyridone (12).
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■ Asymmetric Synthesis of (-)-Norcamphor Using L-Proline Perchlorate
Seiichi Takano,* Hiromitsu Iwata, and Kunio Ogasawara
*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan
Abstract
Asymmetric synthesis of (-)-norcamphor (5) from a nonchiral nortricyclanone (1) and L-proline perchlorate via the iminium perchlorate (2) has been described.
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■ The Reduction of Azafluorenones
Krystian Kloc, Jacek Mlochowski,* and Zdzislaw Szulc
*Institute of Organic and Polymer Technology, Technical University of Wroclow, 50-370 Wroclaw, Poland
Abstract
Treatment of 1- and 4-aza- as well as 1,5-, 1,8-, 2,5-, and 4,5-diazafluorenones with hydrazine hydrate at 160-170 °C led to azafluorenes in the yield 33 - 90%. In the case of 4-aza-, 2,5- and 4,5-diazafluorenone, the dimerization products, 9,9’-bisazafluorenes were also formed under reduction conditions.
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■ Attemped Synthesis of Aporphine Skeleton by Photocyclization of 4,5-Diaryl-4-oxazolin-2-ones
Ichiya Ninomiya,* Ikuko Furutani, Okiko Yamamoto, Toshiko Kiguchi, and Takeaki Naito
*Kobe Women‘s College of Pharmacy, Motoyamakita, Higashinad, Kobe, Hyogo 658, Japan
Abstract
Irradiation of 4,5-diaryl-4-oxazolin-2-ones (la-f) with substituents on a benzene ring and nitrogen afforded various types of phenanthrenes (2a-h). Attempted synthesis of aporphines was undertaken by applying the photocyclization of 4-oxazolin-2-ones (1b,d,e, and f) and (4a and b).
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■ Selective Demethylation of Papaverinol
Somsak Ruchirawat,* Suporn Suparlucknaree, and Noojaree Prasitpan
*Department of Chemistry, Faculty of Science, Mahidol University, Rama 6 Road, Bangkok 10400, Thailand
Abstract
Compound (II), obtained from synthesis, was found to be identical with the product from the reaction of papaverinol with 90% sulphuric acid. 89% Orthophosphoric acid was found to be the acid of choice for the selective demethylation of papaverinol.
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■ Nmr Spectral Assignment of 6,13-Dihydro-5-oxo-5H-isoquinolino[1,2-b][1,3]benzoxazine
Robert John Bass, Michael Kinns, Tetsuji Kametani,* Chu Van Loc, Masataka Ihara, and Keiichiro Fukumoto
*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan
Abstract
A revision of nmr spectral assignment of the title compound is described.
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■ Isobenzofuran
Makhluf J. Haddadin*
*Department of Chemistry, American University of Beirut, Beirut, Lebanon
Abstract
The preparation of isobenzofuran and its thermal and photochemical reactions are reviewed. The chemistry of heterocycles related to isobenzofuran is discussed.
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■ Alkaloids of the Lauraceae
I. Ralph C. Bick* and Wannee Sinchai
*Department of Chemistry, University of Tasmania, GPO Box 252C Hobart, Tasmania, 7001, Australia
Abstract
Alkaloids of the plant family Lauraceae are classified according to structure into fifteen groups, and arranged in tabular form. The genera and species in which they occur are also tabulated, and another table summarises the number of occurrences of each alkaloid group by genus. Incompletely characterised bases not included in these tables are listed separately. Occurrences of the main structural types are compared for the Lauraceae and certain other plant families in a further table. The possible mode of biogenesis of some less familiar bases is discussed, and references are given to the biosynthesis of well-known structural types.