Regular Issue

Vol. 24, No. 8, 1986

40 data found. 1 - 30 listed Next Last
Communication | Regular issue | Vol 24, No. 8, 1986, pp. 2085 - 2088
Published online:
DOI: 10.3987/R-1986-08-2085
Nitriles in Heterocyclic Synthesis: New Approaches for Synthesis of Pyrazoles, Izoxazoles and Pyrimidines

Nadia S. Ibrahim,* Ebtisam A. A. Hafez, and Raafat M. Mohareb

*Department of Chemistry, Faculty of Science, University of Cairo, Giza, Egypt


A variery of pyrazoles and aminoisoxazole were prepared from reaction of N-benzylidene cyanoethanoic hydrazide derivatives with hydrazines and hydroxylamine. A novel pyrimidine synthesis from reaction of ethyl cyanoacetate with the hydrazide is reported.

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Communication | Regular issue | Vol 24, No. 8, 1986, pp. 2089 - 2092
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DOI: 10.3987/R-1986-08-2089
6α/6β-Hydroxy-3-O-methylepimaritidine, Two New Alkaloids from Narcissus tazetta L. var. chinensis Roem

Guang-En Ma,* Hui-Yin Li, Chun-E Lu, Xue-Ming Yang, and Shan-Hai Hong

*Shanghai Institute of Material Media, Chinese Academy of Science, 319, Yue-yang Road, Shanghai, 200031, China


Two new alkaloids, 6α/6β-hydroxy-3-O-methylepimaritidine (3-epipapyramine) (4 and 5) were isolated from the bulbs of Narcissus tazetta L. var. chinensis Roem. together with four known alkaloids, maritidine, 3-O-methylmaritidine, epigalanthamine and lycoramine. The structures of 4 and 5 were determined on the basis of their IR, UV, CD, 1H-NMR and MS fragments.

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Communication | Regular issue | Vol 24, No. 8, 1986, pp. 2093 - 2097
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DOI: 10.3987/R-1986-08-2093
Dechlorination of Chloropyrazine N-Oxides

Yasuo Akita, Akira Inoue, Yohko Mori, and Akihiro Ohta*

*Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan


By heating chloropyrazine N-oxides with palladium catalysts and potassium acetate in N,N-dimethylformamide under a hydrogen stream, the chlorine atom was readily removed without deoxygenation of the N-oxide group.

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Communication | Regular issue | Vol 24, No. 8, 1986, pp. 2099 - 2103
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DOI: 10.3987/R-1986-08-2099
Synthesis of the Enantiomers of 7,8-Dimethoxy-7,8-2-phenyl-1,2,4,5-tetrahydro-3-benzazepine

Jürg R. Pfister*

*Institute of Organic Chemistry, Syntex Research, Palo Alto, California 94304, U.S.A.


The chiral 2-phenyltetrahydro-3-benzazepines (R)-8 and (S)-8 were prepared from optically active O-acetylmandeloyl chlorides utilizing a ring closure/ring opening strategy.

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Communication | Regular issue | Vol 24, No. 8, 1986, pp. 2105 - 2108
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DOI: 10.3987/R-1986-08-2105
Four New C20-Diterpene Alkaloids, Spirasine I, Spirasine II, Spirasine VII and Spirasine VIII from Spiraea japonica

Fang Sun, Xiao-tian Liang,* and De-quan Yu

*Institute of Materia Medica, Chinese Academy of MedicalSceince, Nan-wei Road, Beijing 100050, China


The structures of spirasine I (1), spirasine II (2), spirasine VII (3) and spirasine VIII (4), new C20-diterpene alkaloids isolated from Spiraea japonica, were established on the basis of chemical and spectroscopic evidence and confirmed by X-ray crystallography.

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Communication | Regular issue | Vol 24, No. 8, 1986, pp. 2109 - 2110
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DOI: 10.3987/R-1986-08-2109
Regiospecific Cyclization of 3-Carbomethoxyindole-1-propanoic Acid onto 7-Position of the Indole Nucleus

Shin-ichi Nakatsuka,* Osamu Asano, and Toshio Goto

*Faculty of Agriculture, Gifu University, 1-1 Yanagito, Gifu, Gifu 501-1193, Japan


Intramolecular cycilzation of 3-carbomethoxyindole-1-propanoic acid (3) occurred not onto 2-position but onto 7-position to afford pyrrolo[3,2,1-ij]quinoline derivative 5.

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Communication | Regular issue | Vol 24, No. 8, 1986, pp. 2111 - 2115
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DOI: 10.3987/R-1986-08-2111
Effects of Hetero Atom Substituents in the Decomposition of Pyrazolines: Abnormal Behavior of Methoxy Group Compared with Arylthio or Arylseleno Group

Masashi Hamaguchi,* Toshiya Furusawa, and Toshikazu Nagai

*Institute of Chemistry, College of General Educatin, Osaka University, Toyonaka, Osaka 560-8531, Japan


Quantitative hydrogen migration was observed on the thermal decomposition of 4-methoxy-substituted pyrazolines with two electron-withdrawing groups at C(3) except some trans-5-alkyl-4-methoxypyrazolines accompanied with methoxy migration.

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Communication | Regular issue | Vol 24, No. 8, 1986, pp. 2117 - 2120
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DOI: 10.3987/R-1986-08-2117
A Novel Total Synthesis of (±)-Ajmalicine

Takeaki Naito, Noriko Kojima, Okiko Miyata, and Ichiya Ninomiya*

*Kobe Women’s College of Pharmacy, Motoyamakita, Higashinad, Kobe, Hyogo 658, Japan


A common key intermediate (9) for the synthesis of (±)-ajmalicine was prepared in 11 steps from harmalane (2) with 30% overall yield.

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Communication | Regular issue | Vol 24, No. 8, 1986, pp. 2121 - 2125
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DOI: 10.3987/R-1986-08-2121
A New Route to 1-Acyl-5-oxoperhydroazocine Core Using 1,2,3,5,6,7-Hexahydropyrrolizinium Perchlorates

Seiji Miyano,* Nobuko Mibu, Michiko Irie, and Kunihiro Sumoto

*Faculty of Pharmaceutical Sciences, Fukuoka University, 8-19-1 Nanakuma, Jonan-ku, Fukuoka 814-0180, Japan


A convenient simple method for the synthesis of 1-substituted 5-oxoperhydroazocines (1) is described. The method consists of N-acylation of 5-oxoperhydroazocine which is one of the tautomers of the pseudobase (3) generated by the treatment of 1,2,3,5,6,7-hexahydropyrrolizinium perchlorate with aqueous alkali.

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Communication | Regular issue | Vol 24, No. 8, 1986, pp. 2127 - 2131
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DOI: 10.3987/R-1986-08-2127
Directed beta-Lithiation of 2-Substituted Indoles — A New Synthetic Route to 2,3-Substituted Indoles

David A. Johnson and Gordon W. Gribble*

*Department of Chemistry, Dartmouth College, Hanover, New Hampshire 03775, U.S.A.


Treatment of several N-protected 2-substituted indoles with n-butyllithium at -78°C leads toC-3 lithiation, presumably via coordination with the C-2 substituent. Depending on the exact system, the 3-lithioindole can either be trapped with electrophiles or suffer ring-opening to an alkyne.

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Communication | Regular issue | Vol 24, No. 8, 1986, pp. 2133 - 2136
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DOI: 10.3987/R-1986-08-2133
Phosphono Nucleoside. 2. Synthesis of 1’-Deoxy-1’-phosphono-1-β-D-fructofuranosyluracil and 1’,3’-Dideoxy-1’-phosphono-1-β-D-fructofuranosyluracil

Toshio Tatsuoka,* Kayoko Imao, and Kenji Suzuki

*Suntory Institute for Biochemical Research, Suntory Co. Ltd., 1-1-1, Wakayamadai, Shimamotocho, Mishimagun, Osaka 618-0024, Japan


New phosphono nucleosides, phosphono methyl derivatives of arabinofuranosyl- and of deoxyribofuranosyluracil, substituted at C-1’ position were synthesized.

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Communication | Regular issue | Vol 24, No. 8, 1986, pp. 2137 - 2140
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DOI: 10.3987/R-1986-08-2137
Diels-Alder Reaction of 3-(2-Pyridylsulfinyl)acrylates — The Enhancement of the Reactivity and the Diastereoaelectivity by the Introduction of Electron-withdrawing Substitutents on thr Pyridine Ring

Hiromitusu Takayama, Kazuya Hayashi, Yoshio Takeuchi, and Toru Koizumi*

*Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, 2630 Sugitani, Toyama, Toyama 930-0194, Japan


The introduction of nitro or trifluoromethyl group at C3 position on pyridine ring enhanced the reactivity and the diastereoselectivity of 3-(2-pyridylsulfinyl)acrylate in the Diels-Alder reaction with furan.

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Communication | Regular issue | Vol 24, No. 8, 1986, pp. 2141 - 2145
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DOI: 10.3987/R-1986-08-2141
Kazinol P, a Novel Isoprenylated Spiro-compound from Broussonetia kazinoki Sieb.

Susumu Kato, Yoshio Hano, Toshio Fukai, Yasumi Kosuge, and Taro Nomura*

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


A novel isoprenylated spiro-compound named kazinol P (1) was isolated from a benzene extract of the root bark of Broussonetia kazinoki Sieb. (Japanese name “Himekozo”, Moraceae). The structure was shown to be 1 on the basis of spectral evidence. Kazinol P is regarded biogenetically as a variation of a flavan and/or a 1,3-diphenylpropane derivative, such as kazinol E (2) and kazinol C (6).

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Communication | Regular issue | Vol 24, No. 8, 1986, pp. 2147 - 2150
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DOI: 10.3987/R-1986-08-2147
New Synthrtic Routes to Fully Unsaturated 1,4-Benzodiazepines from Quinolyl Azides

Haruki Sashida, Akira Fujii, Hiroyui Sawanishi, and Takashi Tsuchiya*

*School of Pharmacy, Hokuriku University, 3-Ho, Kanagawa machi, Kanazawa 920-1181, Japan


Photolysis of 4-azidoquinolines (1) in the presence of methoxide ions resulted in ring-expansion to give the 1H-1,4-benzodiazepines (3), which were tautomerized to the 3H-isomers (4) by further treatment with sodium methoxide. Similarly, 3-azidoquinolines (9) afforded the 3H-1,4-benzodiazepines (11), which were converted to the 5H-isomers (14) by treatment with sodium methoxide.

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Communication | Regular issue | Vol 24, No. 8, 1986, pp. 2151 - 2153
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DOI: 10.3987/R-1986-08-2151
A Synthesis of 15,16-Dimethoxyerythirin-6-en-8-one

Yong Zhang, Shigeko Takeda, Takao Kitagawa, and Hiroshi Irie*

*Faculty of Pharmaceutical Sciences, Nagasaki University, 1-14, Bunkyo-machi, Nagasaki 852-8521, Japan


A synthesis of 15,16-dimethoxyerythrin-6-en-8-one was accomplished using an intramolecular Wadsworth-Emmons reaction for constructing five-membered lactam, indicating a convenient method to the synthesis of the erythrinan skeleton.

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Report | Regular issue | Vol 24, No. 8, 1986, pp. 2155 - 2163
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DOI: 10.3987/R-1986-08-2155
Synthesis of (±)-1β-Methoxy-9β,7β-epoxy-5α-methyl-trans-decalin

Ajoy K. Banerjee,* Carmen A. Peña, Hétor E. Hurtado S., and María G. Díaz

*Centro de Química, Instituto Venezolano de Investigaciones Científicas, I.V.I.C., Apartado 21827, Caracas 1020-A, Venezuela


The ketal-ketone (14), prepared from dione (3), was converted to the olefin (16) which on reduction and methylation yielded the ketone (18). The alcohol (19), obtained by reduction with sodium and n-propanol, on oxidation with lead tetraacetate in benzene afforded the cyclic ether (1) which on treatment with trichloromethylsilane and sodium iodide followed by oxidation with Jones reagent produced the keto-ether (2). The α,β-unsaturated ketone (21), prepared from keto-ether (2), was subjected to cyanation, hydrolysis, esterification and deoxygenation respectively to obtain ester (23) whose conversion to lactone (24) followed by reduction, oxidation and esterification afforded the keto-ester (25). The olefinic material obtained from the keto-ester (25) was treated with silver chromate and iodine to obtain α-keto halogenated product and this on treatment with diphosphorous tetraiodide yielded the keto-ester (26).

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Report | Regular issue | Vol 24, No. 8, 1986, pp. 2165 - 2167
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DOI: 10.3987/R-1986-08-2165
Asymmetric Synthesis of Cyclic Imino Acids via Chiral Shiff Bases

Jerzy Bajgrowicz, Abdelrhani El Achquar, Maris-Louise Roumestant, Chiristian Pigière, and Philippe Viallefont*

*U.S.T.L., Place E. Bataillon, 34060 Montpellier Cedex, France


A new method of synthesis af cyclic imino acids is reported. Diastereoselective alkylation of schiff bases (derived from α-amino esters and (+) or (-) 2-hydroxypinan-3-one) with dihalogeno compounds, followed by hydrolytic cleavage and cyclisation affords the imino esters. Reactions are highly enantioselective, with one exception corresponding to steric crowding.

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Report | Regular issue | Vol 24, No. 8, 1986, pp. 2169 - 2172
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DOI: 10.3987/R-1986-08-2169
Improved Procedures for Preparation of 2-Pyridones and 2-Hydroxymethylpyridines from Pyridine N-Oxides

Katsuhiro Konno,* Kimiko Hashimoto, Hatuhisa Shirahama, and Takeshi Matsumoto

*Faculty of Science, Hokkaido University, Kita 10 Nishi 8, Kita-ku, Sapporo, Hokkaido 060-0810, Japan


2-Pyridones and 2-hydroxymethylpyridines were prepared from pyridine N-oxides by treatment with trifluoroacetic anhydride in dimethylformamide. The reaction proceeds at room temperature in satisfactory yields.

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Report | Regular issue | Vol 24, No. 8, 1986, pp. 2173 - 2174
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DOI: 10.3987/R-1986-08-2173
Synthesis of Parasorbic Acid, the Component of Sorbus aukuparia L.

Tsuguo Sato*

*Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan


Parasorbic acid ((5s)-(+)-hexen-5-olide) was synthesized from ethyl acetoacetate by utilizing its baker’s yeast reduction.

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Report | Regular issue | Vol 24, No. 8, 1986, pp. 2175 - 2178
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DOI: 10.3987/R-1986-08-2175
The Reaction of Lithio-alkyk-isoxazoles with Acid Chlorides in the Presence of Cerium Trichloride. Direct Preparation of β-Keto-isoxazolyl Compounds

Nicholas R. Natale,* Steven G. Yocklovich, and Brenda M. Mallet

*Department of Chemistry, University of Idaho, 301 Renfrew Hall, Moscow, ID 83844-2343, U.S.A.


Lithio-alkyl-isoxazoles react with acid chlorides in the presence of cerium trichloride to give β-keto-isoxazoles.

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Paper | Regular issue | Vol 24, No. 8, 1986, pp. 2179 - 2194
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DOI: 10.3987/R-1986-08-2179
Regiospecific Alkylation of 9-Benzyl-1,3-dimethyl-6-hydroxypyrimido[2,1-f]purine-2,4,8(1H,3H,9H)-trione

Daniel M. Solomon, David J. Conn, Shing-Chun Wong, and James J. Kaminski*

*Pharmaceutical Research Division, Schering-Plogh Research Institute, Bloomfield, NJ 07003, U.S.A.


The sodium salt of 9-benzyl-1,3-dimethyl-6-hydroxypyrimido[2,1-f]purine-2,4,8(1H,3H,9H)-trione (1a) reacted with a series of alkyl halides in N,N-dimethylformamide to yield 7-carbon alkylated products (1b-1). No O-alkylated products were detected. Isolated yields (not optimized) were in the range of approximately 15-58% for activated halides; non-activated halides were substantially less reactive and gave lower yields. The effects of reaction parameters on reactivity and site of alkylation are discussed, and it is demonstrated that the observed regiospecificity is not the result of an equilibration process.

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Paper | Regular issue | Vol 24, No. 8, 1986, pp. 2195 - 2200
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DOI: 10.3987/R-1986-08-2195
Heterocycles 4: Synthesis of 2,2-Dimethyl-2H-pyrano[2,3-a]carbazoles

Desikachari Sowmithran and Karnam Jayarampillai Rajendra Prasad*

*Department of Chemistry, Indian Institute of Technology, Powai, Bombay 400 076, India


Condensation of methyl 1-hydroxy-carbazolecarboxylates 1, 2 and 3 with 3,3-dimethylacrylic acid in presence of zinc chloride-phosphorous oxychloride (ZnCl2-POCl3) afforded corresponding 3,4-dihydro-2,2-dimethyl-4-oxo-2H-pyrans, 4,5 and 6 respectively. These on sodium borohydride (NaBH4) reduction followed by dehydration using p-toluenesulphonyl chloride-pyridine yielded 2,2-dimethyl-2H-pyrano[2,3-a]carbazoles, 10, 11 and 12 respectively.

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Paper | Regular issue | Vol 24, No. 8, 1986, pp. 2201 - 2213
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DOI: 10.3987/R-1986-08-2201
Novel Synthesis of Pyridopyrimidine Diones

Amin Farouk Fahmy, Mohamed Salah Kamel Youssef,* Mohamed Said Abdel Halim, Mamdouh Adly Hassan, and Jourgin Sauer

*Chemistry Department, Faculty of Science, Assiut University, Assiut 71516, Egypt


N-(Phenylsulphonyloxy)quinolinimide (I) reacts with different nucleophiles to give II-VIII. It was proved that the nucleophilic attack occurs at the more electro-positive carbonyl group to give only one product in good yields.

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Paper | Regular issue | Vol 24, No. 8, 1986, pp. 2215 - 2218
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DOI: 10.3987/R-1986-08-2215
"Cross-coupling" of 2-Chlorobenzothiazole with Benzothiazolylalkylmagnesium Bromide: Synthesis of Bis(2-benzothiazolyl)alkanes

Francesco Babudri, Saverio Florio,* Giovanni Ingrosso, and Anna Maria Turco

*Laboratorio di Chimica Organica, C.d.L. in Scienze Biologiche, Università, via Monteroni, 73100 Lecee, Italy


Bis(2-benzothiazolyl)alkanes have been prepared via cross-coupling of 2-chlorobenzothiazole with benzothiazolylalkylmagnesium bromide.

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Paper | Regular issue | Vol 24, No. 8, 1986, pp. 2219 - 2225
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DOI: 10.3987/R-1986-08-2219
Synthesis of Limousamine, a 4-Hydroxylated Cularine

Angel Rodriguez de Lera, Carmen Villaverde, and Luis Castedo*

*Departamento de Química Orgánica, Universidad de Santiago and Sección de Alcaloides (C.S.I.C.), E-15706, Santiago de Compostela, Spain


LTA treatment of cularidine 1c as described by Umezawa afforded a 2:3 mixture of limousamine 1a and its 4-epimer 1g, whose stereochemistry is discussed. DDQ oxidation of the O-methyl derivative 1h gave the first 3,4-dioxocularine alkaloid 9.

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Paper | Regular issue | Vol 24, No. 8, 1986, pp. 2227 - 2231
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DOI: 10.3987/R-1986-08-2227
A Simple Efficient Synthesis of a New, Versatile Tetrahydroisoquinoline-1,3-aminoalcohol Synthon

Jenó Kóbor, Ferenc Fülöp, and Gábor Bernáth*

*Institute of Pharmaceutical Chemistry,University of Szeged, H-6720 Szeged, Eötvös u. 6, Hungary


Through the addition of 2 moles of formaldehyde to 1-methyl-6,7-dimethoxy- and 6,7-diethoxy-3,4-dihydroisoquinoline, the corresponding 1-[bis(hydroxymethyl)methyl]-6,7-dialkoxy-3,4-dihydroisoquinolines (3a,b) were prepared, which were then reduced to the 1,3,3’-trifunctional tetrahydroisoquinoline aminoalcohol synthons (5a,b).

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Paper | Regular issue | Vol 24, No. 8, 1986, pp. 2233 - 2237
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DOI: 10.3987/R-1986-08-2233
A Selective Synthesis of Unsymmetrical 1,1’-Methylenebisdiazoles by Solid-liquid Phase Transfer Catalysis

Sebastian Juliá, Carlos Martínez-Martorell, and José Elguero*

*Instituto de Química Médica, C. S. I. C., Calle Juan de Cierva, 3, 28006 Madrid, Spain


1,1’-Methylenebisdiazoles Az1-CH2-Az2, Az1 and Az2 being two different diazoles, can be prepared selectively in three steps, through 1-hydroxymethyl- and 1-chloromethyldiazoles, by solid-liquid (S-L) phase transfer catalysis.

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Paper | Regular issue | Vol 24, No. 8, 1986, pp. 2239 - 2245
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DOI: 10.3987/R-1986-08-2239
Unusual Rearrangement Reaction of Quebrachamine Derivative Catalyzed by Cyanide Anion

Kiyoshi Yoshida, Sumihiro Nomura, Yoshihiko Nishibata, and Yoshio Ban*

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


Cyanation of trimethylammonium salt 8 with potassium cyanide afforded 3-cyano derivatives 9a and 9b accompanied by a significant amount of unexpected rearrangement product 10. The structure of 10 was established by single X-ray crystallographic analysis.

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Paper | Regular issue | Vol 24, No. 8, 1986, pp. 2247 - 2254
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DOI: 10.3987/R-1986-08-2247
Synthesis of Imidazo[1,2-a]pyridine and Pyrido[1,2-a]pyrimidine Derivatives by the Addition and Cyclocondensation Reactions of Ketenaminals Containing Imidazolidine or Hexahydropyrimidine Ring with Esters of α,β-Unsaturated Acids

Zhi-tang Huang* and Zhi-rong Liu

*Institute of Chemistrym, Academia Sinica, Beijing, China


Ketenaminals 1 react with methyl propiolate, methyl acrylate and dimethyl acetylenedicarboxylate to afford the fused imidazo[1,2-a]pyridines and pyrido[1,2-a]pyrimidines 3, 4 and 5, respectively. In some cases, the intermediate addition products 2 and 6b are isolated.

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Paper | Regular issue | Vol 24, No. 8, 1986, pp. 2255 - 2259
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DOI: 10.3987/R-1986-08-2255
Synthesis of Bi- and Tricyclic Mesonic [1,2,4,6]Thiatriazine-1,1,3-trioxides

Jae Sung Kang and Dong Young Oh*

*Department of Applied Chemistry, Korea Advanced Institute of Science and Technology, P.O.Box 150 Chong-Yang-ni, Seoul 131, Korea


The reaction of N-substituted aminoheterocycles with chlorosulfonyl isocyanate (CSI) or pentachlorophenyl N-chlorosulfonylcarbamate (PCPCSC) affords bi- and tricyclic mesoionic [1,2,4,6]thiatriazine-1,1,3-trioxides in the presence of ethyldiisopropylamine.

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40 data found. 1 - 30 listed Next Last