Regular Issue

Vol. 45, No. 5, 1997

19 data found. 1 - 19 listed
Communication | Regular issue | Vol 45, No. 5, 1997, pp. 835 - 839
Published online:
DOI: 10.3987/COM-97-7764
C2-Alkylaminopenem Synthesis

Takumi Yamasaki, Hiroshi Kadoi, and Isao Nagakura*

*Chemical Process Development Laboratory, Drug Substance Manufacturing Plant, Pfizer Pharmaceuticals, 5-Gochi, Taketoyo-cho, Chita-gun, Aichi, Japan


A simple synthesis of C2-dialkylaminopenems is described. Azetidione glyoxylate has been cyclized to C2-aminopenem, via an intramolecular sulfide-contraction reaction.

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Communication | Regular issue | Vol 45, No. 5, 1997, pp. 841 - 845
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DOI: 10.3987/COM-97-7767
Convenient Preparation of 1-Azaazulene Derivatives by the Reaction of Tropon-imines with Enamines

Makoto Nitta* and Tohru Takayasu

*Department of Chemistry, School of Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku-ku, Tokyo 169-8555, Japan


Troponimines having OH, OMe, OMs, and OTs group on the nitrogen atom react with pyrrolidine enamines to give formal [8+2] cycloadducts, which undergo spontaneous aromatization to give 1-azaazulene derivatives in good to moderate yield.

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Communication | Regular issue | Vol 45, No. 5, 1997, pp. 847 - 850
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DOI: 10.3987/COM-97-7774
Novel Cyclizatoin of Unsaturated Alcohols by Phenyl Selenocyanate in the Presence of Copper Bis-(trifluoromethanesulfonate)

Hirofumi Inoue and Shizuaki Murata*

*Graduate School of Human Informatics, Nagoya University, Nagoya 464-8601, Japan


Intramolecular oxyselenenylation of unsaturated alcohols by phenyl selenocyanate with copper bis(trifluoromethanesulfonate) proceeds stereoselectively to give cyclic ethers.

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Communication | Regular issue | Vol 45, No. 5, 1997, pp. 851 - 855
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DOI: 10.3987/COM-97-7777
Novel Heterocyclic Enediynes. Molecular Design, Chemical Synthesis and DNA Cleavage

Kazunobu Toshima,* Kiyoshi Ohishi, Miho Tomishima, and Shuichi Matsumura

*Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Hiyoshi, Kohoku-ku Yokohama 223-8522, Japan


The novel 10-membered oxaenediyne (4a) and azaenediynes (5a-d) were designed and synthesized in a short procedure, and the azaenediynes (5a-d) were found to effectively cleave DNA under both weakly acidic and basic conditions with no additive.

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Communication | Regular issue | Vol 45, No. 5, 1997, pp. 857 - 861
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DOI: 10.3987/COM-97-7783
Imidazo[4,5-e][1,2,4]triazocine: A Novel 5:8-Fused Ring System Riddled With Rearrangements

Friedrick N. Burnett and Ramachandra S. Hosmane*

*Laboratory for Drug Design and Synthesis, Department of Chemistry and Biochemistry, University of Maryland Baltimore County, 1000 Hilltop Circle, Baltimore, Maryland 21228, U.S.A.


Attempts to synthesize the title 5:8-fused heterocyclic ring system resulted in a number of novel opportunistic rearrangements and transformations. There is, however, some evidence to believe that one of these rearrangements might proceed through the transient intermediacy of this ring system.

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Communication | Regular issue | Vol 45, No. 5, 1997, pp. 863 - 866
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DOI: 10.3987/COM-97-7790
Triethylborane-mediated Atom Transfer Cyclization of N-Allylic α-Iodo-acetamides: A Convenient Synthesis of β-Iodomethyl-γ-lactams

Masazumi Ikeda, Hirotaka Teranishi, Noriko Iwamura, and Hiroyuki Ishibashi*

*Faculty of Pharmaceutical Scicences, Kanazawa University, 13-1 Takara-machi, Kanazawa 920-0934, Japan


In the presence of triethylborane, N-allylic α-iodoacetamides underwent atom tranfer cyclization to give β-iodomethyl-γ-lactams in high yields.

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Communication | Regular issue | Vol 45, No. 5, 1997, pp. 867 - 874
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DOI: 10.3987/COM-97-7794
Revised Structure of Sanggenon A

Yoshio Hano, Ryuichi Kanzaki, Toshio Fukai, and Taro Nomura*

*Faculty of Pharmaceutical Sciences, Toho University, 2-2-1, Miyama, Funabashi, Chiba 274-8510, Japan


The structure of sanggenon A, which has been isolated from the Chinese crude drug "Sang-Bai-Pi", was revised on the basis of two-dimentional NMR spectroscopic and chemical evidence. Sanggenon A is a unique 3-hydroxyflavanone derivative bearing an isoprenyl group at the C-2 position of the skeleton. The other flavanones having sanggenon A-type structure, including sanggenons M and C, also required the revision of the structure.

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Paper | Regular issue | Vol 45, No. 5, 1997, pp. 875 - 888
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DOI: 10.3987/COM-96-7672
Synthesis of N-Substituted 2,4-Diaminothiazoles and Their Salts

Ronald Flaig and Horst Hartmann*

*Fachbereich Chemie und Umweltingenieurwesen, Fachhochschule Merseburg, Geusaer Str., D-06217 Merseburg, Germany


A series of N(2),N(4)-subsituted 2,4-diaminothiazoles (22) and their corresponding mineral acid salts (22·HX) and (22·2HX) have been prepared by the reaction of POCl3 with N-substituted S-(dialkylaminocarbonylmethylene)isothiouronium salts (20) available from corresponding substituted thioureas (18) and N,N-disubstituted chloroacetamides (19) or by the reaction of primary or secondary amines (25) in excess with N(2)-unsubstituted or N(2)-disubstituted 2-amino-4-thiazolinimine hydrochlorides (24) availabe by the reaction of corresponding N-substituted thioureas (18) with chloroacetonitirle (23).

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Paper | Regular issue | Vol 45, No. 5, 1997, pp. 889 - 896
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DOI: 10.3987/COM-96-7683
Reaction of Aryl Bromomethyl Ketone Phenylsulfonylhydrazones with Benzylideneaniline

Suketaka Ito,* Akikazu Kakehi, Kyoko Okada, Saori Goto, and Hiroshige Kawaguchi

*Depatment of Indusrial Chemistry, Faculty of Engineering, Shinshu University, 4-17-1 Wakasato, Nagano 380-8553, Japan


6-Aryl-3,4-diphenyl-2-phenylsulfonyl-2,3,4,5-tetrahydro-1,2,4-triazines and 4-aryl-1-phenyl-1,2,3-triazoles were obtained in moderate yields by the reaction of aryl bromomethyl ketone phenylsulfonylhydrazones with benzylidnenaniline.

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Paper | Regular issue | Vol 45, No. 5, 1997, pp. 897 - 910
Published online:
DOI: 10.3987/COM-96-7696
A Novel Method of Preparation of 3-Acylimidazo[1,2-a]pyridines

Jean-Luc Moutou, Martine Schmitt, Valérie Collot, and Jean-Jacques Bourguignon*

*Laboratoire de Pharmacochimie Moleculaire, Faculte de Pharmacie, ULP, 74, route du Rhin 67401 ILLKIRCH Cedex, France


A series of 2-substituted 3-acylimidazo[1,2-a]pyridines were synthesized in good to moderate yields from secondary amidino ketones and bromine in acetic acid. Cyclocondensation of the α-bromo-β-amidino ketones (6) led to the corresponding trans-dihydroimidazoles (13), which may yield spontaneously the stable 3-acylimidazo[1,2-a]pyridines (2) after dehydrogenation.

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Paper | Regular issue | Vol 45, No. 5, 1997, pp. 911 - 914
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DOI: 10.3987/COM-97-7751
(3aR*,6aS*)-5,5-Diphenyl-2,3,3a,4,6,6a-hexahydrosilolano[3,4-b]furan-2-one: A New Fused γ-Butyrolactone

Dominique Damour, Gilles Doerflinger, and Serge Mignani*

*Rhône-Poulenc Rorer S.A., Centre de Recherche de Vitry-Alfortville, 13 Quai Jules Guesde, BP 14, 94403, Vitry-sur-Seine Cedex, France


The title fused γ-butyrolactone (1) was prepared in four steps, starting from 1,1-diphenyl-1-silacyclopent-3-ene.

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Paper | Regular issue | Vol 45, No. 5, 1997, pp. 915 - 925
Published online:
DOI: 10.3987/COM-97-7755
Coriacyclodienin and Coriacycloenin: Two New Annonaceous Acetogenins from Annona coriacea

Edna Lucia Meneses Da Silva, François Roblot, and André Cavé*

*Faculté de Pharmacie, Laboratoire de Pharmacognosie, URA 1843 CNRS (BIOCIS), 5 rue J.B. Clément 92296 Châtenay-Malabry Cedex, France


Two new Annonaceous acetogenins, coriacyclodienin (1) and coriacycloenin (2), have been isolated from the roots of Annona coriacea Mart. (Annonaceae). 1 is the first mono-THF acetogenin which bears two double bonds in the aliphatic chain, which 2 has the same mono-THF ring and only one double bond. Both compounds (1) and (2) were oxidized and cyclized, in a one pot reaction, to give the mixtures of the four possible stereoisomer derivatives (3, 4, 5 and 6) of 1 and the two possible stereoisomer derivatives (7 and 8) of 2. The absolute stereochemistries of 1 and 2 were assigned using NMR analysis of their Mosher esters and enzymatic method.

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Paper | Regular issue | Vol 45, No. 5, 1997, pp. 927 - 942
Published online:
DOI: 10.3987/COM-97-7760
2-[Arylamino(imino)]perhydropyrido-[1,2-d][1,3,4]oxadiazine and 2-[Aryl-amino(imino)]-perhydropyrrolo[1,2-d]-[1,3,4]oxadiazine: Heterocyclic Ring Systems Involving a Bridge-Head Nitrogen

Ari Rosling, Ferenc Fülöp, Reijo Sillanpää, and Jorma Mattinen*

*Department of Organic Chemistry, Åbo Akademi University, Biskopsgatan 8, FIN-20500 Åbo, Finland


Hydrazino alcohols (1 - 4) were converted with phenyl or 4-chlorophenyl isothiocyanate into their thiourea derivatives (5a,b, 6a,b, 9a,b and 10a,b) which then were cyclized by treatment with methyl iodide and alkali to furnish 2-[arylamino(imino)]perhydropyrido[1,2-d][1,3,4]oxadiazines (7a,b) and perhydropyrrolo[1,2-d][1,3,4]oxadiazines (12a,b) and their 2-arylimino-3N-methyl derivatives (8a,b and 13b). The nmr spectra and X-ray crystallographic analysis indicated that the 1,3,4-oxadiazines adopt rigid cis- or trans-fused ring conformations, depending on the parent ring size and the 3N-substituent. It was found that in the unsubstituted 1,3,4-oxadiazines (7a,b and 12a,b) involving a potential tautomeric equilibrium. The amino form is most likely to predominate.

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Note | Regular issue | Vol 45, No. 5, 1997, pp. 943 - 948
Published online:
DOI: 10.3987/COM-96-7685
Synthetic Route to α-Phosphono-γ-butyrolactones: Synthesis of γ-Substituted α-Methylene-γ-butyro-lactones

Chi-Wan Lee, Jun Mo Gil, and Dong Young Oh*

*Department of Chemistry, Korea Advanced Institute of Science and Technology, 373-1, Kusung-Dong, Yusung-Gu, Taejon, 305-701, Korea


Treatment of lithiated homoallylic phosphonates wiht dimethyl carbamyl chloride gave 2-amidophosphonate derivatives. A solution of 2-amidophosphonate in DME-H2O (2:1 vol) reacted with 2 eq. iodine at room temperature to give α-phosphono-γ-iodoalkyl-γ-butyrolactones in good yield, although the products are mixture. Wadsworth-Emmons reaction of α-phosphono-γ-iodoalkyl-γ-butyrolactones with aldehydes gave α-(alkyl)methylene-γ-iodoalkyl-γ-butyrolactone derivatives.

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Note | Regular issue | Vol 45, No. 5, 1997, pp. 949 - 954
Published online:
DOI: 10.3987/COM-96-7723
The Thermal Dimerization of Pyrano[3,2-c]coumarins

Giovanni Appendino, Giovanni Palmisano,* Silvia Tagliapietra, Gian Mario Nano, Luisella Calabi, and Lino Paleari

*Dipartimento di Scienza, Tecnologia del Farmaco, via P. Giuria 9, I-10125 Torino, Italy


The thermal dimerization of the pyrano[3,2-c]coumarin (1) gave a mixture of four dimeric compounds, whose structure was established by extensive NMR studies.

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Note | Regular issue | Vol 45, No. 5, 1997, pp. 955 - 962
Published online:
DOI: 10.3987/COM-97-7744
An Original Way for Synthesis of New Nitrobenzothiadiazole Derivatives

Patrice Vanelle,* Céline Tremblais Liegeois, Jacobine Meuche, José Maldonado, and Michel P. Crozet

*Laboratorie de Chimie Organique, Université d' Aix-Marseille 2, Faculté de Pharmacie, 27 Bd. Moulin, 13385 Marseille Cedex 05, France


The C-alkylation reaction of 4-chloromethyl-7-nitro-2,1,3-benzothiadiazole with 2-nitropropane anion which is shown to proceed by an SRN1 mechanism is an original way for the synthesis of new 2,1,3-benzothiadiazoles.

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Note | Regular issue | Vol 45, No. 5, 1997, pp. 963 - 967
Published online:
DOI: 10.3987/COM-97-7773
Model Study for the Construction of C Ring of Pimara Type Diterpenes

Takashi Fukumoto, Minoru Oguchi, Yoshinobu Kashibuchi, and Tadahiro Kato*

*Department of Chemistry, Faculty of Science, Science University of Tokyo, Kagurazaka 1-3, Shinjuku-ku, Tokyo 162-8601, Japan


As the model experiment to explore the construction route of our synthetic intermediate (8), the epoxy alcohol (5) was prepared by Sharpless epoxidation including asymmetric introduction of the epoxide ring. The cyclization of 5 to the diol (6) proceeded in 40% yield by the action of Ti(OiPr)4 at room temperature. The diol (6) having more than 90% enantiomeric excess was obtained from the asymmetric epoxide (5).

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Note | Regular issue | Vol 45, No. 5, 1997, pp. 969 - 973
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DOI: 10.3987/COM-97-7786
Pyrano- and Furocarbazole Alkaloids from the Root Bark of Clausena excavata

Tian-Shung Wu,* Shiow-Chyn Huang, and Pei-Lin Wu

*Department of Chemistry, Natioanl Cheng Kung University, Tainan, 70101, Taiwan, R.O.C.


Two pyranocarbazole alkaloids, clausine-W (1) and clausine-T (2), as well as two furocarbazole alkaloids, furoclausine-A (3) and furoclausine-B (4), were isolated and identified from the acetone extract of the root bark of Clausena excavata. Their structures have been elucidated by spectroscopoic analyses.

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Review | Regular issue | Vol 45, No. 5, 1997, pp. 975 - 1011
Published online:
DOI: 10.3987/REV-97-488
Furopyridines. Synthesis and Properties

Shunsaku Shiotani*

*Department of Chemistry, Faculty of Science, Toyama University, Gofuku 3190, Toyama 930, Japan


This review describes the synthesis of the frameworks of furo[2,3-b]-, -[3,2-b]-, -[2,3-c]- and -[3,2-c] pyridine, and reactions of the furopyridines: such as bromination, nitration, H-D exchange and lithiation at the furan ring, chlorination, acetoxylation and cyanation of the N-oxides of furopyridines and 2,3-dihydrofuropyridines, and conversion of each substituent into other functional groups.

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19 data found. 1 - 19 listed