Regular Issue

Vol. 55, No. 6, 2001

24 data found. 1 - 24 listed
Communication | Regular issue | Vol 55, No. 6, 2001, pp. 1015 - 1018
Published online:
DOI: 10.3987/COM-01-9195
Acid-catalyzed Photorearrangement of the Bond-switching Isomer of a Pentamethylcyclooctapyrimidine-2,4-dione

Kazue Ohkura, Ken-ichi Nishijima, Shun Uchiyama, Akiyo Sakushima, and Koh-ichi Seki*

*Faculty of Pharmaceutical Sciences, Health Sciences University of Hokkaido, Ishikari-Tobetsu, Hokkaido 061-0293, Japan


UV-irradiation of the tautomer (4c) of 1,3,6,8,10-pentamethylcyclooctapyrimidine-2,4-dione (1c) in the presence of TFA gives 9, 11-diazapentacyclo[,3.02,6.04,8]dodecane (5) and pentaleno[2,1-d]pyrimidine (6).

PDF (196KB)
Communication | Regular issue | Vol 55, No. 6, 2001, pp. 1019 - 1022
Published online:
DOI: 10.3987/COM-01-9211
Montmorillonite KSF-Mediated Facile Synthesis of Pyrroles

Susanta Samajdar, Frederick F. Becker, and Bimal K. Banik*

*The University of Texas, M. D. Anderson Cancer Center, Department of Molecular Pathology, Box 89, 1515 Holcolmbe Blvd, Houston, TX 77030, U.S.A


A facile synthesis of substituted pyrroles over montmorrilonite KSF clay has been accomplished in excellent yield.

PDF (25KB)
Communication | Regular issue | Vol 55, No. 6, 2001, pp. 1023 - 1028
Published online:
DOI: 10.3987/COM-01-9222
Combinatorial Synthesis of Nikkomycin Analogues on Solid Support

Atsushi Suda, Atsunori Ohta, Masayuki Sudoh, Takuo Tsukuda,* and Nobuo Shimma

*Combination Chemistry Group, Department of Chemsitry, Nippon Roche K.K. Research Center, 200 Kajiwara, kamakura, Kanagawa 247-8530, Japan


Synthesis of nikkomycin analogue library by combinatorial synthesis on solid support and evaluation of their enzyme inhibitory activity against Candida albicans chitin synthases are described.

PDF (53KB)
Paper | Regular issue | Vol 55, No. 6, 2001, pp. 1029 - 1043
Published online:
DOI: 10.3987/COM-01-9177
A Formal Synthesis of (±)-Eseroline via an Azaoxy-Cope Rearrangement

Paulo F. Santos, Paulo S. Almeida, Ana M. Lobo,* and Sundaresan Prabhakar*

*Chemistry Department, Center for Fine Chemistry and Biotechnology, Faculty of Sciences and Technology, New University of Lisbon, 2825-114 Monte de Caparica, Portugal


A novel synthesis of (±)-desoxyeseroline, from the crucial oxindole (15), obtained by a 3,3-sigmatropic rearrangement of the enolate derived from the hydroxamic acid derivative (5) followed by radical desulfurisation, has been described. The requisite C2N fragment has been introduced through a Michael addition of nitroethylene to 15.

PDF (358KB)
Paper | Regular issue | Vol 55, No. 6, 2001, pp. 1045 - 1056
Published online:
DOI: 10.3987/COM-01-9180
Semisynthetic Dimers of Antiparkinsonic Ergot Alkaloids

Vladimír Kren,* Lenka Weignerová, Marek Kuzma, Alexandr Jegorov, and Petr Sedmera

*Institute of Microbiology, Laboratory of Biotransformation, Academy of Sciences of the Czech Republic, Vídenská 1083, CZ 142 20 Prague 4, Czech Republic


1,1-Linked dimers of semisynthetic ergoline alkaloids with antiparkinsonic activity were prepared in 60 - 63% yield from the parent compounds (pergolide, terguride) by action of α,ω-dihalogenalkanes in DMSO/KOH. N-1-ω-Halogenalkyl pergolide and terguride precursors were used for the synthesis of non-symmetric dimers. N-6 Alkylation was achieved (yield 18 - 28%) using 1,6-dihalogenohexane in DMF/K2CO3.

PDF (177KB)
Paper | Regular issue | Vol 55, No. 6, 2001, pp. 1057 - 1062
Published online:
DOI: 10.3987/COM-01-9183
Oxidation of 2-Amino-2’-hydroxybenzophenone N-Acylhydrazones: Synthesis of 6-Substituted Dibenzazepin-11-ones

Antigoni Kotali,* Efthymia Lazaridou, Vassilios P. Papageorgiou, and Philip A. Harris

*GlaxoSmithKline,Five Moore Drive, P.O. Box 13398, Research Triangle Park, North Carolina, 27709-3398, U.S.A.


The synthesis of 6-substituted 11H-dibenz[b,e]azepin-11-ones is reported via the lead tetraacetate oxidative cyclization of 2-amino-2-hydroxybenzophenone N-acylhydrazones. A mechanism involving formation of a 2-acyl-2’-aminobenzophenone intermediate is proposedA

PDF (42KB)
Paper | Regular issue | Vol 55, No. 6, 2001, pp. 1063 - 1070
Published online:
DOI: 10.3987/COM-01-9188
Palladium Catalyzed Carbonylative Cross-Coupling Reaction of Indolylborates with Prop-2-ynyl Carbonates

Minoru Ishikura,* Harue Uchiyama, and Noriyuki Matsuzaki

*Faculty of Pharmaceutical Sciences, Health Sciences University of Hokkaido, Ishikari-Tobetsu, Hokkaido 061-0293, Japan


Palladium catalyzed carbonylative cross-coupling reaction of 1-methylindolylborate (2a) with prop-2-ynyl carbonates (3) produced cyclopenta[b]indole derivatives in a one-pot manner. Hence, the use of indolylborates (2c, d) for the reaction with 3 allowed the isolation of indol-2-yl allenyl ketones (4).

PDF (344KB)
Paper | Regular issue | Vol 55, No. 6, 2001, pp. 1071 - 1080
Published online:
DOI: 10.3987/COM-01-9191
Electrochemistry of Aminoazines and Nitrones: Electrochemical Reductions of 2-Amino-1,4-pyrazine with Nitrones to Form Amide Compounds and Electrochemical Oxidations of Anilines with Nitrones to Form Imine Compounds and Benzaldehydes

Katsuhiro Saito,* Ayako Kawamura, Takashi Kanie, Yosuke Ueda, and Satoru Kondo

*Department of Applied Chemistry, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya 466-8555, Japan


Electrochemical reductions of 2-amino-1,4-pyrazine in the presence of nitrone derivatives afforded two types of amide compounds, one of which was derived from both the pyrazine and the nitrones and the other from only the nitrones. The analogous reactions but using 2-aminopyridine or aniline instead of the pyrazine resulted in the recovery of the starting materials. On the other hand, electrochemical oxidations of the aminoazine derivatives in the presence of nitrones did not afford any isolatable products. However, the reaction using aniline derivatives formed imine compounds accompanied by benzaldehyde derivatives.

PDF (74KB)
Paper | Regular issue | Vol 55, No. 6, 2001, pp. 1081 - 1093
Published online:
DOI: 10.3987/COM-01-9197
Synthetic Approaches to 4,8-Dimethyl-4’-(N-pyridinium-methyl)-4’,5’-dihydropsoralens and Their Activity against PAM 212 Keratinocytes

Marilyn Whittemore, Ned Heindel,* Christophe Guillon, Thomas McNeel, Robert Rapp, Thomas Mariano, Diane Heck, and Jeffrey Laskin

*Buckman Laboratories International, INC., 1256 Norh McLean Blvd. Memphis, TN 38108, U.S.A.


Synthetic approaches to novel 4,8-dimethyl-4’-halomethyl-4’,5’-dihydropsoralens as synthetic precursors to 4,8-dimethyl-4’-(N-pyridiniummethyl)-4’,5’-dihydropsoralens are described. The compounds are potential therapeutic agents for improved psoralen ultraviolet radiation therapy with reduced mutagenicity.

PDF (72KB)
Paper | Regular issue | Vol 55, No. 6, 2001, pp. 1095 - 1103
Published online:
DOI: 10.3987/COM-01-9199
Studies toward Unique Mycolactone Macrolides from Mycobacterium ulcerans

Mukund K. Gurjar* and Joseph Cherian

*Division of Organic Chemistry (Synthesis), National Chemical Laboratory, Pune 411 008, India


The synthesis of C1’- C19’ segments of mycolactones A and B with well defined stereochemical centers at C-12’, C-13’ and C-15’ has been described.

PDF (129KB)
Paper | Regular issue | Vol 55, No. 6, 2001, pp. 1105 - 1111
Published online:
DOI: 10.3987/COM-01-9200
New Synthetic Approach to Pyridazino[4,5-b]indoles by Pd(0)-catalyzed Cross-Coupling Reaction

Gábor Krajsovszky, Péter Mátyus, Zsuzsanna Riedl, Dorottya Csányi, and György Hajós

*Chemical Research Center, Institute of Chemistry, Hungarian Academy of Sciences, H-1525 Budapest, P.O.Box 17, Hungary


5-Iodo-2-methylpyridazin-3(2H)-one readily underwent Suzuki coupling with protected anilinoboronic acids to yield the corresponding arylpyridazinones which proved to be suitable starting compounds to a ring closure — a 4 step pathway — to pyridazino[4,5-b]indoles.

PDF (113KB)
Paper | Regular issue | Vol 55, No. 6, 2001, pp. 1113 - 1119
Published online:
DOI: 10.3987/COM-01-9201
Reductive Amination of 1-[3-(2- Alkylbenzofuranyl)]-2-phenylethanones. Synthesis of 1-[3- (2-Alkylbenzofuranyl)]-2-phenylethylamines

Halina Kwiecién* and Irena Bogdanska

*Department of Organic Synthesis, Technical University of Szczecin, Al.Piastów 17, 71-065 Szczecin, Poland


1-[3-(2-Alkylbenzofuranyl)]-2-phenylethylamines were prepared by reduction of 1-[3-(2-alkylbenzofuranyl)]-2-phenylethanone azines with amalgamated aluminum. Two isomeric azines were separated from products of reaction of 1-[3-(2-alkylbenzofuranyl)]-2-phenylethanones with hydrazine hydrate in ethanol solution. On the other hand, instead of desired amine, aziridine derivative was obtained by reduction of the mixture of (Z)- and (E)-1-[3-(2-butylbenzofuranyl)-2-(4-methoxyphenyl)]ethanone oximes with lithium aluminum hydride. The reduction of 1-[3-(2-butylbenzofuranyl)]-2-phenylethanone hydrazone with aluminium lead up to the corresponding imine.

PDF (116KB)
Note | Regular issue | Vol 55, No. 6, 2001, pp. 1121 - 1125
Published online:
DOI: 10.3987/COM-01-9184
A New 12a-Hydroxyelliptone from the Stems of Derris malaccensis

Nopporn Thasana, Mayuree Chuankamnerdkarn, and Somsak Ruchirawat*

*Labotratory of Medicinal Chemistry, Chulabhorn Reseach Institute, Vipavadee-Rangsit Highway, Bangkok 10210, Thailand


A new rotenoid, 12a-hydroxyelliptone (1) and the known rotenoid 12-deoxo-12α-acetoxyelliptone (2) were isolated from the stems of Derris malaccensis. The structures were established by spectroscopic and chemical methods as well as by comparison with published data.

PDF (39KB)
Note | Regular issue | Vol 55, No. 6, 2001, pp. 1127 - 1132
Published online:
DOI: 10.3987/COM-01-9187
Tandem Cyclization of Phytosphingosine

Su Yeon Jo, Hyoung Cheul Kim, Dong Ju Jeon, and Hyoung Rae Kim*

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


Phytosphingosine is easily cyclized during the protection of amino group with phthalic acid derivatives to form trisubstituted tetrahydrofuran structure (2) by the attack of 4-hydroxyl group to the terminal carbon. The structure of compound (2) was confirmed by X-Ray crystallography and synthetic method.

PDF (76KB)
Note | Regular issue | Vol 55, No. 6, 2001, pp. 1133 - 1140
Published online:
DOI: 10.3987/COM-01-9189
13C-NMR as Useful Tool for Unambiguous Identification of Ring Substituted N1(2)(3)-Alkylbenzotriazole Isomers

Antonio Carta,* Paolo Sanna, Giuseppe Paglietti, and Fabio Sparatore

*Dipartimento Farmaco Chimico Tossicologico, University of Sassari, Via Muroni 23/A, 07100 Sassari, Italy


Analysis of the chemical shifts of C-3a and C-7a angular atoms in the benzotriazoles bearing a substituent on the ring and an alkyl group on the nitrogen position of the triazole moiety proved to be a good tool for identification of the different N-alkyl isomers.

PDF (51KB)
Note | Regular issue | Vol 55, No. 6, 2001, pp. 1141 - 1145
Published online:
DOI: 10.3987/COM-01-9190
A New Neoclerodane Diterpenoid from Scutellaria hematochlora

Yoshio Takeda,* Satomi Tateoka, Toshiya Masuda, Hideaki Otsuka, Gisho Honda, Yoshihisa Takaishi, Michiho Ito, Olimjon K. Khodzhimatov, and Ozodbek A. Ashurmetov

*Faculty of Integrated Arts and Sciences, University of Tokushima, Minamijosanjima-cho, Tokushima 770-0814, Japan


From the aerial parts of Scutellaria hematochlora, a new neoclerodane diterpenoid, hematochloridin (1) was isolated together with acetovanillon, vanillin, apigenin and sitosterol 3-O-glucoside. The structure of the new compound was elucidated by spectral analyses.

PDF (177KB)
Note | Regular issue | Vol 55, No. 6, 2001, pp. 1147 - 1149
Published online:
DOI: 10.3987/COM-01-9194
An Improved Hydrolysis of 7α-Chloro-7β-cyano-6,14-endo-ethenotetrahydrothebaine to Its 7-Oxo Derivative

Dean Y. Maeda and Andrew Coop*

*Department of Pharmceutcial Sciences, School of Pharmacy, University of Maryland, 20 Norht Pine Street, Baltimore, MD 21201, U.S.A.


An efficient method for the conversion of 7α-chloro-7β-cyano-6,14-endo-ethenotetrahydrothebaine (4) to 6,14-endo-etheno-7-oxotetrahydrothebaine (3) using Na2S·9H2O is described. This method requires no chromatography for purification, and is therefore amenable to large scale preparation of the potentially important opioid intermediate.

PDF (33KB)
Note | Regular issue | Vol 55, No. 6, 2001, pp. 1151 - 1159
Published online:
DOI: 10.3987/COM-01-9198
Nucleophilic Substitution Reaction of 1-Methoxy-6-nitroindole

Koji Yamada, Toshiya Kawasaki, Tomomi Fujita, and Masanori Somei*

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


Nucleophilic substitution reaction of 1-methoxy-6-nitroindole (1) was examined. In the reaction with sodium methoxide or sodium cyanide as a nucleophile, 2- and 3-methoxy-6-nitroindoles, and 7-cyano-6-nitroindole were obtained, respectively. A novel methylene homologation at the 3-position was found in the reaction of 1 with sodium methyl sulfide or potassium salt of diethyl malonate to give 3-methylthiomethyl-6-nitroindole and its 2-methylthio derivative, and diethyl 2-(6-nitroindol-3-yl)methylmalonate, respectively. Possible reaction mechanism is discussed.

PDF (108KB)
Note | Regular issue | Vol 55, No. 6, 2001, pp. 1161 - 1163
Published online:
DOI: 10.3987/COM-01-9202
The First Example of Synthesis of Tetracyano Derivatives of Thianthrene and Phenoxathiin with Use of Thioacetamide

Igor' G. Abramov,* Alexey V. Smirnov, Sergey A. Ivanovsky, Marina B. Abramova, and Vladimir V. Plakhtinskii

*Yaroslavl State Technical University, Moscowsky Prospekt 88, 150023 Yaroslavl, Russia


New cyano derivatives of thianthrene and phenoxathiin have been synthesized by aromatic nucleophilic substitution reaction of the bromine atom and nitro group in 4-bromo-5-nitrophthalonitrile.

PDF (93KB)
Note | Regular issue | Vol 55, No. 6, 2001, pp. 1165 - 1171
Published online:
DOI: 10.3987/COM-01-9203
A Concise Formal Synthesis of (±)-Deplancheine

Takashi Itoh, Yûji Matsuya, Yasuko Enomoto, and Akio Ohsawa*

*School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan


For the purpose of verifying the utility of both enantiomers of 1-allyl-1,2,3,4-tetrahydro-β-carboline in alkaloid synthesis, the racemic one was transformed to (±)-deplancheine in 10 steps in 11% overall yield.

PDF (256KB)
Note | Regular issue | Vol 55, No. 6, 2001, pp. 1173 - 1179
Published online:
DOI: 10.3987/COM-01-9206
Diastereoselective Iodoamidation of 3-Acetoxybut-1-enylamines: Synthesis of 3-Acetoxy-4-iodo-2-(p-methoxybenzyl)pyrrolidines

Kyu-Tae Chang, Ki Chang Jang, Ho-Yong Park, Young-Kook Kim, Ki Hun Park,* and Woo Song Lee*

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


3α-Acetoxy-4α-iodo-2α-(p-methoxybenzyl)pyrrolidine (2) and its enanti-omer (3) were synthesized via diastereoselective iodoamidation, starting from D- or L-tyrosine. The key step contains unfavorable 5-endo-trig cyclization and the diastereoselective addition of ethynylmagnesium bromide to aldehydes (9) by the chelation-controlled Cram cyclic model.

PDF (164KB)
Note | Regular issue | Vol 55, No. 6, 2001, pp. 1181 - 1188
Published online:
DOI: 10.3987/COM-01-9219
Facile Preparation of 1,3-Selenazine Derivatives by Reaction of Primary Selenoamides with α,β-Unsaturated Aldehydes of in the Presence of BF3ÅEEt2O

Mamoru Koketsu,* Yuichi Takenaka, Sohma Hiramatsu, and Hideharu Ishihara*

*Department of Chemistry, Faculty of Engineering, Gifu University, 1-1 Yanagito, Gifu, Gifu 501-1193, Japan


Various 1,3-selenazine derivatives were synthesized by the reaction of primary selenoamides with α,β-unsaturated aldehydes in the presence of BF3·Et2O.

PDF (54KB)
Note | Regular issue | Vol 55, No. 6, 2001, pp. 1189 - 1194
Published online:
DOI: 10.3987/COM-01-9224
Reaction of 2-Chloro-1-azaazulene with Diphenylcyclopropenone; Dimerization of the Cycloadduct Attended by cine-Substitution and Rearrangement

Noritaka Abe,* Hiroyuki Fujii, and Akikazu Kakehi

*Department of Chemistry, Faculty of Science, Yamaguchi University, 1677-1 Yoshida, Yamaguchi 753-8512, Japan


2-Chloro-1-azaazulene reacted with diphenylcyclopropenone to give 3,4-diphenyl-2a,5-dihydro-2H-2a-azabenz[cd]azulene-2,5-dione and 6-[(3,4-diphenyl-5-oxo-2a,5-dihydro-2H-2a-azabenz[cd]azulen-2-ylidene)-methyl]-3,4-diphenyl-2a,5-dihydro-2a-azaacenaphtylen-5-one; the latter would be produced via cycloaddition and a successive cine-substitution followed by rearrangement.

PDF (222KB)
Note | Regular issue | Vol 55, No. 6, 2001, pp. 1195 - 1199
Published online:
DOI: 10.3987/COM-01-9225
6-Hydroxycyanidin 3-Malonylglucoside from the Flowers of Alstromeria ‘Tiara

Fumi Tatsuzawa, Naho Murata, Koichi Shinoda, Norio Saito, Atsushi Shigihara, and Toshio Honda*

*Faculty of Pharmaceutical Sciences, Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, Japan


A novel malonylanthocyanin was isolated from the flowers of Alstroemeria ‘Tiara’ and determined to be 6-hydroxycyanidin 3-O-[6-O-malonyl-β-D-glucopyranoside].

PDF (81KB)
24 data found. 1 - 24 listed