Regular Issue

Vol. 9, No. 9, 1978

13 data found. 1 - 13 listed
Communication | Regular issue | Vol 9, No. 9, 1978, pp. 1197 - 1206
Published online:
DOI: 10.3987/R-1978-09-1197
Synthesis of 3-Isoquinolines

Hiroshi Fukumi* and Hideshi Kurihara

*Medicinal Chemistry Research Laboratories, Sankyo Co., Ltd., 1-2-58 Hiromachi, Shinagawa-ku, Tokyo 140-8710, Japan


Treatment of N-benzyl-diethoxyacetamides and N-alkyl-N-benzyl-diethoxyacetamides with sulfuric acid afforded the corresponding 3-isoquinolinols and 2-alkyl-3-isoquinolones, respectively. This reaction is regarded as a kind of Pomeranz-Fritsch synthesis.

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Communication | Regular issue | Vol 9, No. 9, 1978, pp. 1207 - 1216
Published online:
DOI: 10.3987/R-1978-09-1207
Unusual Formation of Oxazoles by Base- or Acid-catalyzed Ring Opening of 2-Acyl-2H-azirines

Kazuaki Isomura, Youichi Hirose, Hideo Shuyama, Sumiko Abe, Gen-ichiro Ayabe, and Hiroshi Taniguchi*

*Research Institute of Industrial Science, Faculty of Engineering, Kyushu University, 6-1, Kasuga-koen, Kasuga 816-8580, Japan


Formation of 2-acyl-2H-azirines was confirmed in thermolyses of β-acylvinyl azides to establish the generality of azirine formation from vinyl azides. Unusual C-C bond fission of 3-unsubstituted 2-acyl-2H-azirine to give oxazole was found to be a base catalyzed reaction. On the other hand, 3-substituted analogues were found to undergo acid-catalyzed reaction to give oxazoles.

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Communication | Regular issue | Vol 9, No. 9, 1978, pp. 1217 - 1222
Published online:
DOI: 10.3987/R-1978-09-1217
The Reaction of 4-Chloroquinoline 1-Oxide with Activated Acetylenes: Furo[3,2-c]quinolines

Persephone Canonne,* Gilles Lemay, and Rudolph A. Abramovitch

*Département de Chimie, Faculté des Sciences et de Génie, Université Laval, Cité Universitaire, Québec, G1K 7P4, Canada


4-Chloroquinoline 1-oxide and ethyl phenylpropiolate in boiling toluene give a mixture of 2- and 3-keto-alkylated products as well as ethyl 2-phenylfuro[3,2-c]quinoline-3-carboxylate. With ethyl acetylenedicarboxylate only low yields of the 2-keto-alkylated product and of the furoquinoline were formed. This is to be contrasted with the observation that 4-chloropyridine 1-oxide and phenylcyanoacetylene or ethyl phenylpropiolate give high yields of the corresponding furopyridine.

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Communication | Regular issue | Vol 9, No. 9, 1978, pp. 1223 - 1231
Published online:
DOI: 10.3987/R-1978-09-1223
Thiaole N-Oxides from 2-Dialkylamino-1,3-oxathiolium Cation

Kentaro Hirai* and Teruyuki Ishiba

*Shionogi Research Laboratories, Shionogi & Co. Ltd., Fukushima-ku, Osaka 553-0002, Japan


Reaction of hydroxylamine with 2-dialkylamino-5-phenyl-1,3-oxathiolium cation gave ω-(dialkylamino-oximinomercapto)acetophenone which was readily cyclized to afford 2-dialkylamino-4-phenylthiazole-3-oxide hydrochloride by ethanolic hydrochloric acid.

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Communication | Regular issue | Vol 9, No. 9, 1978, pp. 1233 - 1240
Published online:
DOI: 10.3987/R-1978-09-1233
Synthesis of Hypecorine and Hypecorinine Analogs from 3,4-Dihydropapaverine

Vilím Simánek,* Vladimír Preininger, Frantisek Grambel, and Ladislav Dolejs

*Institute of Medical Chemistry, Palacky University, 3, Hnevotínská, 775 15 Olomouc, Czech Republic


Reaction of 2’-hydroxymethyl-2-methyl-3,4-dihydropapaverinium (10) and α-oxo-2’-hydroxymethyl-2-methyl- 3,4-dihydropapaverinium salts (11) with hydroxide ions gives cyclic pseudobases 12 and 13, analogs of the alkaloids hypecorine (1) and hypecorinine (2). Derivatives of 2-methylpapaverinium salts form pseudobases by addition of hydroxide ions to immonium bond. Biogenetic conclusions are given.

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Communication | Regular issue | Vol 9, No. 9, 1978, pp. 1241 - 1247
Published online:
DOI: 10.3987/R-1978-09-1241
Ambiguine and Dihydroajaconine: Two New Diterpenoid Alkaloids from Consolida ambigua

S. William Pelletier,* Rajinder S. Sawhney, and Naresh V. Mody

*Department of Chemistry, Institute for Natural Products Research, The University of Georgia, Chemistry Building, Athens, Georgia 30602-2556, U.S.A.


Chemical investigation of the minor alkaloids of Consolida ambigua has led to the isolation and characterization of two new diterpenoid alkoloids, ambiguine (1) and dihydroajaconine (7). Ambiguine is the first lycoctonine-type alkaloid in which a methoxy group is present at the C(8)-position, and dihydroajaconine is a reduced form of the known alkaloid, ajaconine.

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Communication | Regular issue | Vol 9, No. 9, 1978, pp. 1249 - 1255
Published online:
DOI: 10.3987/R-1978-09-1249
A New Route to (±)-cis-2-Oxabicyclo[3.3.0]oct-6-en-3-one, a Prostaglandin Synthon

Seiichi Takano,* Hiromitsu Iwata, and Kunio Ogasawara

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan


A new route to (±)-cis-2-oxabicyclo[3.3.0]oct-6-en-3-one (1), an important prostaglandin synthon, has been developed using a symmetrical starting material (3).

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Communication | Regular issue | Vol 9, No. 9, 1978, pp. 1257 - 1261
Published online:
DOI: 10.3987/R-1978-09-1257
[2,3]Sigmatropic Rearrangement of N-Substituted Quaternary Salts of Diethyl Pyrrolidinomethylphosphonate

Shinzo Kano,* Satoshi Hibino, and Yasuyuki Tanaka

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


The base-catalyzed rearrangement of N-benzyl-N-diethylphosphonomethylpyrrolidinium bromide (2) was investigated to afford the diethyl pyrrolidinobenzylphosphonate (3). In a similar fassion, the quarternary salts (4) and (6) were converted to the corresponding substituted diethyl pyrrolidinomethylphosphonates (5) and (7), respectively. Condensation of 3 with anisaldehyde, followed by hydrolysis of the resulting enamine (8) yielded 4-methoxybenzyl 2-methylphenyl ketone (9).

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Communication | Regular issue | Vol 9, No. 9, 1978, pp. 1263 - 1269
Published online:
DOI: 10.3987/R-1978-09-1263
An Approach to the Skeleton of Rauwolfia Alkaloids. A General Synthesis of 3,8-Epoxy-7-keto-6-oxabicyclo[3.2.1]octane Derivatives

Toshio Suzuki, Akiko Tomino, Seiko Kagaya, Katsuo Unno, and Tetsuji Kametani*

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan


Hydrolysis of the Diels-Alder adducts (1) and (2), followed by halolactonization, gave 4-bromo- (6) and 4-iodo-3-methoxycarbonyloxymethyl-3,8-epoxy-7-keto-6-oxabicyclo[3.2.1]octane-2-carboxylic acid (8), respectively. Arndt-Eistert reaction of the acid chloride (14), derived from 6, provided the methyl ester (16). The intermediate diazoketone (15) was also transformed to the amides (17) and (18) by condensation with tryptamine and 6-methoxytryptamine, respectively, both of which would be key intermediates for the synthesis of Rauwolfia alkaloids, deserpidine (12) and reserpine (13).

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Communication | Regular issue | Vol 9, No. 9, 1978, pp. 1271 - 1275
Published online:
DOI: 10.3987/R-1978-09-1271
Oxazoles in Organic Synthesis: Some Observations on the Use of 5-Alkoxyoxazoles in the Diels-Alder Process

Alan P. Kozikowski* and Kimiaki Isobe

*Department of Chemistry, University of Pittsburgh, Parkman Avenue & University Drive, Pittsburgh, PA 15260 , U.S.A.


The preparation and Diels-Alder reactivity of 5-ethoxy-2-carboethoxyoxazole and its derivatives have been examined. As a consequence of this investigation, a simple procedure for the preparation of 5-ethoxyoxazole has been discovered.

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Report | Regular issue | Vol 9, No. 9, 1978, pp. 1277 - 1285
Published online:
DOI: 10.3987/R-1978-09-1277
Studies on Potential Antitumor Agents (III). Synthesis of 4-Arylcyclophosphamides

Yun-Er Shih, Jy-Shih Wang, and Chao-Tung Chen*

*Institutue of Chemistry, Academia Sinica, 128, Yan-Chiu-Yuan Road, Sec II, Nankang, Taipei,11529, Taiwan, R.O.C.


Nine cis-trans pairs of 4-arylcyclophosphamides have been synthesized from benzaldehydes in three steps. Structures were assigned based on infrared spectra.

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Report | Regular issue | Vol 9, No. 9, 1978, pp. 1287 - 1294
Published online:
DOI: 10.3987/R-1978-09-1287
Studies in Protoberberibe Alkaloids. XVI. NMR Spectral Studies of 10,11-Dioxygenated 13-Methyltetrahydroprotoberberines

Bantwal R. Pai,* Kuppuswamy Nagarajan, Hosbett Suguna, and Sankaran Natarajan

*Department of Chemistry, Presidency College, Madras 600005, India


The NNR chemical shift differences of protons at C13a and C8 and the methyl protons at C13 of cis- and trans-fused 10,11-dioxygenated 13-methyltetrahydroprotoberberines are discussed.

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Report | Regular issue | Vol 9, No. 9, 1978, pp. 1295 - 1300
Published online:
DOI: 10.3987/R-1978-09-1295
Kuwanon E, a New Flavanone Derivatives from the Root Bark of the Cultivated Mulberry Tree (Morus alba L.)

Taro Nomura* and Toshio Fukai

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


A new flavanone derivative named kuwanon E was isolated from the root bark of the cultivated mulberry tree (a variety of Morus alba L.). The structure was presumed to be 5,7,2’,4’-tetrahydroxy-5’-geranylflavanone (I) by spectral data.

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13 data found. 1 - 13 listed