Regular Issue

Vol. 48, No. 2, 1998

19 data found. 1 - 19 listed
Communication | Regular issue | Vol 48, No. 2, 1998, pp. 215 - 219
Published online:
DOI: 10.3987/COM-97-8032
o-Nitrophenyltriflates in Quinoline Synthesis: Easy Access to a Streptonigrin Synthon

Cedric W. Holzapfel* and Catherine Dwyer

*Department of Chemistry and Biochemistry, Rand Afrikaans University, P.O. Box 524, Auckland Park, 2006, Johanesberg, South Africa


An efficient route to a wide range of 2-hydroxyquinolines from o-nitrophenyltriflates via a Heck reaction is reported, with emphasis on the preparation of a synthetic equivalent of the streptonigrin AB ring system

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Communication | Regular issue | Vol 48, No. 2, 1998, pp. 221 - 226
Published online:
DOI: 10.3987/COM-97-8041
A Facile Method for Direct Conversion of Dihydrofuroquinolones to Dihydropyrroloquinolones

Sung Soo Kim,* Hyae Gyeong Cheon, Seung Kyu Kang, Eul Kgun Yum, and Joong-Kwon Choi

*Bio-Organic Division, Korea Research Institute of Chemical Technology, P. O. Box 107, Yusong, Taejon 305-606, Korea


A novel and efficient method is described for one-step conversion of dihydrofuroquinolones to dihydropyrroloquinolones in high yields under mild conditions.

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Communication | Regular issue | Vol 48, No. 2, 1998, pp. 227 - 234
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DOI: 10.3987/COM-97-8052
Exclusive cis-1,4-Addition Reaction in the Bromination of 2,5-Bis(trimethylsilyl)-thiophene Monooxide

Shao-Zhong Zhang, Soichi Sato, Ernst Horn, and Naomichi Furukawa*

*Tukuba Advanced Research Alliance Center, Department of Chemistry, University of Tsukuba, 1-1-1 Ten-nodai, Tsukuba-shi, Ibaraki, 305-8571, Japan


2,5-Bis(trimethylsilyl)thiophene monooxide (1) underwent a 1,4-addition reaction with Br2 to give stereospecifically 2,5-bis(trimethylsilyl)-2,5-cis-dibromothiolene monooxide (2) in quantitative yield.

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Communication | Regular issue | Vol 48, No. 2, 1998, pp. 235 - 238
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DOI: 10.3987/COM-97-8055
Synthesis of the A/B/C Ring System of Taxane Diterpenes from (S)-(+)-Carvone

Yoshimasa Hirai, Kennosuke Ito, and Hiroto Nagaoka*

*Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan


A new route for the synthesis of the tricyclo[,8]pentadecane skeleton, the A/B/C ring system of taxanes, via epoxide (12) from (S)-(+)-carvone using sequential Michael reaction followed by base-induced oxy-Cope rearrangement and Diels-Alder reaction is described.

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Communication | Regular issue | Vol 48, No. 2, 1998, pp. 239 - 242
Published online:
DOI: 10.3987/COM-97-8056
Concise and Versatile Syntheses of N-Arylalkylpiperidines as Potential Intermediates for 4-Anilidopiperidine Analgesics

Young-Ger Suh,* Dong-Yun Shin, Kyung-Ho Cho, and Jae-Sang Ryu

*College of Pharmacy, Seoul National University, Shillim-Dong, San 56-1, Kwanak-Gu, Seoul 151-742, Korea


N-Arylalkylpiperidones and N-arylalkylspiroepoxypiperidine as potential intermediates for 4-anilidopiperidine analgesics and their structural analogues have been efficiently synthesized from the simple arylalkylamines by two and three step sequences respectively.

Paper | Regular issue | Vol 48, No. 2, 1998, pp. 243 - 248
Published online:
DOI: 10.3987/COM-97-7921
A Facile Access to Benzo[c]phenanthridines via 4-Functionalized 3-Arylisoquinolines

Teresa Vicente, Esther Domínguez,* and María Jesús Villa

*Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Pais, Vasco, P.O. Box 644, 48080-Bilbao, Basque Country, Spain


4b,10b-trans-N-Benzyltetrahydrobenzo[c]phenanthridines have been synthesized by a short and efficient route from a 4-functionalized 3-aryltetrahydroisoquinoline. The 3-aryl-4-carboxymethyltetrahydroisoquinoline (5) and 4-formylmethyl derivative (7) were cyclodehydrated to the corresponding tetracycles.

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Paper | Regular issue | Vol 48, No. 2, 1998, pp. 249 - 257
Published online:
DOI: 10.3987/COM-97-8001
Synthesis of Vinca Alkaloids and Related Compounds XCI. Synthesis of Isolarutensine

András Lukács, Lajos Szabó, Eszter Baitz-Gács, András Dobó, György Kalaus, and Csaba Szántay*

*Institute for Organic Chemistry, Technical University Budapest, H-1521 Budapest, P.O. Box 91Gellért tér 4, Hungary


The synthesis of isolarutensine was elaborated from the mixture of enamines (3a) and (3b).

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Paper | Regular issue | Vol 48, No. 2, 1998, pp. 259 - 266
Published online:
DOI: 10.3987/COM-97-8015
Synthesis of Thieno[3,2-d][1,2,3]-thiadiazoles. New Mechanistic Aspects of the Hurd-Mori Reaction

Peter Stanetty* and Manfred Kremslehner

*Institute of Organic Chemistry, Vienna University of Technology, Getreidemarkt 9/154, A-1060 Vienna, Austria


The synthesis of new thieno[3,2-d][1,2,3]thiadiazole derivatives is described. A modified reaction mechanism of the Hurd-Mori reaction is presented showing better agreement with the obtained results.

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Paper | Regular issue | Vol 48, No. 2, 1998, pp. 267 - 283
Published online:
DOI: 10.3987/COM-97-8023
Synthesis of trans-4a-Aryl-6-oxo-decahydroisoquinolines

Kuniaki Kawamura, Koji Kawai, Toru Miyamoto, Koji Ooshima, and Hiroshi Nagase*

*Basic Research Laboratories, Toray Industries, Inc., 111, Tebiro, Kamakura, Kanagawa, 248, Japan


General and short synthesis of trans-4a-aryl-6-oxodecahydroisoquinolines was described. In particular, the synthesis of 2-cyclopropylmethyl-4a-(3-hydroxyphenyl)-trans-6-oxodecahydroisoquinoline (12), one of the remarkably useful molecule as an opioid message structural part, was attained in only seven steps. The key step in this synthetic approach was 1,4-conjugate addition of aryl moiety to sterically hindered enones (2).

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Paper | Regular issue | Vol 48, No. 2, 1998, pp. 285 - 294
Published online:
DOI: 10.3987/COM-97-8053
The Dakin-West Reaction of N-Acyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylic Acids Using Trifluoroacetic Anhydride: Structural Revision for the Unexpected Product

Masami Kawase,* Youichi Okada, and Hiroshi Miyamae

*Faculty of Pharmaceutical Sciences, Josai University, 1-1 Keyakidai, Sakado, Saitama 350-0295, Japana


The Dakin-West reaction of N-pivaloyl- and N-benzoyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acids (1a-e) with trifluoroacetic anhydride yielded unexpectedly 1-(1-acyloxy-2,2,2-trifluoroethyl)-3,4-dihydroisoquinoline derivatives (3a-e) in good yields. Among of the products (3), the structure of 3b has been confirmed by X-Ray crystallography. The carbamate derivatives (1h, i) gave 1-trifluoroacetyl-N-acyl-1,2,3,4-tetrahydroisoquinolines (4e, f), the Dakin-West reaction products, as a main product. The reaction of N-acetyl derivative (1g) produced completely different type of the product (5).

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Paper | Regular issue | Vol 48, No. 2, 1998, pp. 295 - 302
Published online:
DOI: 10.3987/COM-97-8054
Unsymmetrically S-Substituted Ketene Dithioacetals

Alan R. Katritzky,* Zuoquan Wang, and Scott A. Henderson

*Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, U.S.A.


A novel synthesis of unsymmetrically S-substituted ketene dithioacetals (6a-e) and (7b-e) via the benzotriazole derivatives (5a-e) is described.

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Note | Regular issue | Vol 48, No. 2, 1998, pp. 303 - 310
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DOI: 10.3987/COM-97-7996
Synthesis of Novel 3-Aminobenz[c,d]-indol-2(1H)-ones via Tandem Addition-Rearrangement Aryne Pathway

Anlai Wang, Hongming Zhang, and Ed Biehl*

*Department of Chemistry, Southern Methodist University, P.O.Box 750314, Dallas, Texas 75275-0314, U.S.A.


The reaction of p-methoxyphenylacetonitrile (3) with 2-bromobenzoic acid (1) and LDA gave 7-amino-6,8-bis-(4’-methoxyphenyl)benz[c,d]indol-2(1H)-one (4) and 2-cyano-3-(4-methoxyphenyl)methyl benzoic acid (5). However, treatment of 3 with 2-bromo-4-methylbenzoic acid (12) and LiTMP yielded 5-phenyl-7-amino-6,8-bis-(4’-methoxyphenyl)benz[c,d]indol-2(1H)-one (13). The structure of 4 was established by single-crystal X-Ray diffractometry.

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Note | Regular issue | Vol 48, No. 2, 1998, pp. 311 - 317
Published online:
DOI: 10.3987/COM-97-8028
New Alkaloids from the Root of Stephania tetrandra (Fen-Fang-Ji)

Tatsunori Ogino,* Takao Katsuhara, Toshitsugu Sato, Hiroshi Sasaki, Minoru Okada, and Masao Maruno

*Central Research Laboratory, Tsumura & Co., 3586 Yoshiwara, Ami-machi, Inashiki-gun, Ibaraki, 300-11, Japan


Four new alkaloids named fenfangjines F, G, H, and I were isolated from the root of Stephania tetrandra S. Moore, the Chinise traditional medicine "Fen-Fang-Ji". The chemical structures of fenfangjines F, G, H, and I were determined to be 1, 2, 3, and 4 by spectral analyses and chemical methods, respectively.

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Note | Regular issue | Vol 48, No. 2, 1998, pp. 319 - 328
Published online:
DOI: 10.3987/COM-97-8038
Synthesis of 2,4-Diaminoquinazoline Derivatives

Wojciech Zielinski,* Agnieszka Kudelko, and Elizabeth M. Holt

*Instiute of Organic Chemistry and Technology, Silesian University of Technology, ul. Krzywoustego 4, 44-101 Gliwice, Poland


A series of 6- and 7-substituted derivatives of 2-(N,N-diethylamino)-4-(N,N-dimethylamino)quinazoline have been synthesized. The synthesis consists in converting N-phenyl-N’,N’-diethylurea into chloroamidines which are treated with N,N-dimethylcyanamide to 1-chloro-2,4-diaza-1,3-butadiene derivatives, followed by a cyclization to quinazoline derivatives.

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Note | Regular issue | Vol 48, No. 2, 1998, pp. 329 - 334
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DOI: 10.3987/COM-97-8040
Stereoselective Synthesis of Steroidal Spiroaminotriazine Thiones

Shamsuzzaman,* Anwar Salim, and M. Khursheed Akram

*Department of Chemistry, Jamia Millia Islamia, New Delhi-110 025, India


Stereoselective transformations of some steroidal ketone thiocarbohydrazones (4)-(6) in to the corresponding R-spiroaminotriazine thiones (7)-(9) by their oxidative cyclization with H2O2 at 0 °C are described.

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Note | Regular issue | Vol 48, No. 2, 1998, pp. 335 - 346
Published online:
DOI: 10.3987/COM-97-8044
Synthesis of Pyrrolidinothieno-(or [1]Benzothieno)[3]azepinones from the Corresponding Azepinediones or N-(Thienyl or [1]Benzothienyl)-acetylprolinals

Mohamed Othman, Pierre Netchitaïlo, and Bernard Decroix*

*Laboratoire de Chimie, Faculté des Sciences et Techniques, Université du Havre, 25, rue Philippe Lebon, BP 540, 76600 Le Havre Cedex, France


Synthesis of pyrrolidinothieno (or [1]benzothieno)[3]azepines from the corresponding azepinediones or by direct cyclization of N-[thienyl(or [1]benzothienyl)]acetylprolinals.

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Note | Regular issue | Vol 48, No. 2, 1998, pp. 347 - 351
Published online:
DOI: 10.3987/COM-97-8058
Synthesis and Complexation Behavior of N,N '-Bis(9-anthrylmethyl)-1,4,10,13-tetraoxo-7,16-diazacyclooctadecane

Kanji Kubo,* Ryoichi Ishige, and Tadamitsu Sakurai

*Departmnet of Applied Chemistry, Faculty of Engineering, Kanagawa University, 3-27-1 Rokkakubashi, Kanagawa-ku, Yokohama 221-8686, Japan


Fluorescent photoinduced electron transfer (PET) sensor (3) that consists of diaza-18-crown-6 and 9-anthryl pendant shows fluorescent enhancement with various metal ions. The sensor (3) exhibited K+ selectivity and in the presence of this cation the host fluorescence intensity was increased by a factor of 24.

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Note | Regular issue | Vol 48, No. 2, 1998, pp. 353 - 358
Published online:
DOI: 10.3987/COM-97-8062
Synthesis of 5,6,7,8-Tetrahydro-2H-1-benzopyran-2,5-diones and 1,5-Dihydro-2H-pyrrol-2-ones

Irena Music, Amalija Golobic, and Bojan Vercek*

*Faculty of Chemistry and Chemical Technology, University of Ljubljana, Askerceva 5, P.O. Box 537, SLO-1000 Ljubljana, Slovenia


The use of 2-benzoylamino-3-chloropropenoic acid in the synthesis of 5,6,7,8-tetrahydro-2H-benzopyran-2,5-diones and 1,5-dihydro-2H-pyrrolo-2-ones is reported.

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Review | Regular issue | Vol 48, No. 2, 1998, pp. 359 - 390
Published online:
DOI: 10.3987/REV-97-494
The Dimroth Rearrangement in the Adenine Series: A Review Updated

Tozo Fujii* and Taisuke Itaya

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


Advances in the Dimroth rearrangement in the adenine series are reviewed with 212 reference citations.

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19 data found. 1 - 19 listed