HETEROCYCLES
An International Journal for Reviews and Communications in Heterocyclic ChemistryWeb Edition ISSN: 1881-0942
Published online by The Japan Institute of Heterocyclic Chemistry
Regular Issue
Vol. 19, No. 6, 1982
Published online:
■ Biomimetic Approach to Potential Benzodiazepine Agonists and Antagonists
Michael Cain, Fil Guzman, James M. Cook, Kenner C. Rice, and Phil Skolnick
*Department of Chemistry, University of Wisconsin-Milwaukee, Milwaukee, Wisconsin 53201, U.S.A.
Abstract
A series of heterocycles have been prepared via the Pictet-Spengler reaction and several of these (β-carbolines 2-8, isoquinoline 11a and imidazopyridine derivative 16b) have been found to bind to the benzodiazepine receptor in vitro with moderate to high affinity.
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■ The Use of Nuclear Magnetic Resonance Nulcear Overhauser Enhancements in the Structural Elucidation of Bisbenzylisoquinoline Alkaloids
Héléne Guinaudeau, Bruce K. Cassels, and Maurice Shamma
*Department of Chemistry, The Pennsylvania State University, York Campus, P1031 Edgecomb Avenue, York, Pennsylvania 17403, U.S.A.
Abstract
The new bisbenzylisoquinoline alkaloid (+)-temuconine (1) has been found in Berberis valdiviana Phil. (Berberidaceae). Its structure was confirmed by an NMR NOE study.
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■ Synthesis of 3,3,5-Trimethoxy-2-pyrrolidinone and Its Derivatives
Yoshiyuki Kosugi, Fumiko Hamaguchi, Tatsuo Nagasaka, Sadao Ohki, and Hiroyuki Kikuchi
*School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan
Abstract
A convenient synthesis of 3,3,5-trimethoxy-2-pyrrolidinone (11a-c) by using a reaction of α-halo-β-formylacrylic acid [3-halo-5-hydroxy-2(5H)-furanone] (3a-d) with alkoxide is described. An investigation for synthesis of 2,3-pyrrolidinediones is also mentioned.
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■ Rearrangement of N-Hydroxy-2-azetidinones to 5-Isoxazolidinones
Tohru Hirose, Katsumi Chiba, Shinsaku Mishio, Junji Nakano, and Hitoshi Uno
*Dainippon Pharmaceutical Co., LTD., Enoki 33-94, Suita, Osaka 564, Japan
Abstract
N-Hydroxy-2-azetidinodes (IV) underwent a new rearrangement to 5-isoxazolidinones (V). By use of this rearrangement, one (Ve) of isomers of cycloserine was synthesized.
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■ Synthetic Studies on Carbapenem Antibiotics: A Carbon-introduced Reaction at the C-4 Position of a β-Lactam by Carbane Insertion Reaction
Tetsuji Kametani, Naoaki Kanaya, Tomoko Mochizuki, and Toshio Honda
*Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, Japan
Abstract
The reaction of 4-thia-azetidinones with diazomalonates in the presence of a catalytic amount of rhodium (II) acetate afforded the carbon-introduced products at the C4-position of β-lactams.
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■ A Synthesis of Benzo[b]naphthoi[2,3-d]thiophene Derivatives via Benzo[b]thiophene-2,3-quinodimethane Intermediates
Shinzo Kano, Naoki Mochizuki, Yoko Yuasa, Satoshi Hibino, and Shiroshi Shibuya
*School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan
Abstract
2-Methyl- and 2-ethyl-3-(α-aryl)hydroxymetylbenzo[b]thiophene (6a)-(6d) were heated at 400 °C for 5 min to yield the corresponding benzo[b]naphtho[2,3-d]thiophene derivatives (9a)-(9d), respectively, In a similar fashion, the alcohol (8a) gave 5-methylbenzo[b]naphtho[2,3-d]thiophene (9e) and 5,10-dimethyl derivative (3). 8-Methoxy-5-methyl- (9f) and 5-phenyl derivative (9g) were obtained from the corresponding alcohols (8b) and (8c), respectively.
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■ A Simple Preparation of 2-Aryl-4H-3,1-benzoxazin-4-ones
Eleftherios P. Papadopoulos and Catherine D. Torres
*Department of Chemistry, University of New Orleans, New Orleans, LA 70148, U.S.A.
Abstract
Room temperature treatment of methyl N-acylanthranilates with concentrated sulfuric acid leads to 2-aryl-4H-3,1-benzoxazin-4-ones in excellent yield.
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■ Photolysis of Pyridyl, Quinolyl, and Isoquinolyl Azides in Hydrohalogenoic Acids
Hiroyuki Sawanishi, Toyoko Hirai, and Takashi Tsuchiya
*School of Pharmacy, Hokuriku University, 3-Ho, Kanagawa machi, Kanazawa 920-1181, Japan
Abstract
Photolysis of 4-azido-pyridine and -quinoline in hydrohalogenoic acids gave the 3-amino-4-halogeno compounds (2) via azirine or azacycloheptatetraene intermediates, whereas their N-oxides (4), under similar conditions, gave the 4-amino-3-halogeno compounds (5) presumably via nitrenium ion intermediates. In the 3-azidoquinoline and 4-azidoisoquinoline series, both free bases (6a, 8a) and N-oxides (6b, 8b) gave similar results to 4-azidopyridine and -quinoline N-oxides (4).
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■ Acridone Alkaloids IV. Structures of Four New Acridone Alkaloids from Glycosmis citrifolia (Willd.) Lindl
Tian-Shung Wu, Hiroshi Furukawa, and Chang-Sheng Kuoh
*Faculty of Pharmacy, Meijo University, 150 Yagotoyama, Tenpaku, Nagoya 468-8503, Japan
Abstract
Four new acridone alkaloids, glyfoline (2a), glycocitrine-I (4), -II (5a) and its O-methyl ether (5b) were isolated from the root- and stem-bark of Glycosmis citrifolia, and characterized. Glyfoline (2a) is the most oxygenated acridone alkaloid from natural sources.
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■ Biosynthesis of Averufin and Sterigmatocystin in Aspergillus parasiticus and A. versicolor: Application of Multiple Labelled Acetate in Polyketide Biosynthesis
Ushio Sankawa, Hisao Shimada, Tsutomu Kobayashi, Yutaka Ebizuka, Yoshikuni Yamamoto, Hiroshi Noguchi, and Haruo Seto
*Faculty of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
Abstract
The biosynthesis of averufin and sterigmatocystin was studied by using [2-13C,2-2H3]- and [1-13C,18O2]-acetate as precursors. The patterns of 2H and 18O incorporation suggested new machanisms for the formation of dihydrobisfuran ring and xanthone skeleton.
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■ A General Synthesis of 5-(Alkylamino)-1-β-D-ribofuranosylimidazole-4-carboxamides
Taisuke Itaya, Tohru Saito, Tsunehiro Harada, Seiya Kagatani, and Tozo Fujii
*Faculty of Pharmaceutical Scicences, Kanazawa University, 13-1 Takara-machi, Kanazawa 920-0934, Japan
Abstract
Alkylation of N’-benzyloxy-5-formamido-1-β-D-ribofuranosylimidazole-4-carboxamidine (IV) in the presence of K2CO3 followed by hydrogenolysis of the N’-benzyloxy group and alkaline hydrolysis produced the title compounds (X), intermediates adaptable to the syntheses of various 3-alkyl-9-β-D-ribofuranosylpurines.
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■ Dicyanofuroxan and Hydrazine or Hydroxylamine
Joseph H. Boyer and T. Perumal Pillai
*Department of Chemistry, University of Illinois at Chicago, 845 West Taylor St., Chicago, IL 60607-7061, U.S.A.
Abstract
Dicyanofuroxan combined with hydrazine to produce 1,4-diamino[4,5-c]pyridazinofuroxan (or an imine tautomer 2a) and with hydroxylamine to produce the imine 2b of 1-oxo-4-amino[4,5-c]oxazinofuroxan; mild thermolysis of the latter adduct gave 3(4)-cyano-4(3)-carbamoylfuroxan 8.
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■ Synthesis of 8H-Dibenzo[a,g]quinolizin-8-ones from Homophthalic Anhydrides and 1-Chloroisoquinolines or Isoquinoline N-Oxides. A New Synthesis of Caseadine
Vassil I. Ognyanov, Marietta A. Haimova, and Nikola M. Mollov
*Department of Chemistry, University of Sofia, Sofia 1126, Bulgaria
Abstract
The homophthalic anhydrides 1a,b react with the 1-chloroisoquinolines 2a,b to give the 8H-dibenzo[a,g]quinolizin-8-ones 3a,b,c in high yields. The same products 3a,c are obtained from the isoquinoline N-oxides 6a,b and 1a,b in the presence of acetic anhydride. 3c is converted into the tetrahydroprotoberberine alkaloid (±)-caseadine in two steps.
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■ A New and Facile Synthesis of 5-Arylpyrimidines and 4-Arylpyrazoles
Shinzo Kano, Yoko Yuasa, Shiroshi Shibuya, and Satoshi Hibino
*School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan
Abstract
A condensation of 2-aryl-3-(methylthio)acroleins (3a) -(3e), a new masked form of arylmalondialdehydes, with amidines yielded the corresponding 5-arylpyrimidines (4a)-(4k). Similarly, the reaction of 3 with N-substituted hydrazines gave the corresponding 1-substituted 4-arylpyrzolones (5a) - (5j).
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■ Six-membered Mesoionic Heterocycles of the m-Quinodimethane Dianion Type
Willy Friedrichsen, Thomas Kappe, and Andreas Böttcher
*Institut für Organische Chemie, Universität Kiel, Olshausenstrasse. 40, D-24098 Kiel, Germany
Abstract
In this review is brought together the chemistry of six-membered mesoionic heterocycles which can be derived formally from the m-quinodimethane dianion.
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■ Proton Magnetic Resonance Spectra of Phenothiazine Deivatives
Sayeed Saraf, Muhammad Akram Khan, and Saleh Al-Mousawi
*Department of Chemistry, Faculty of Science, University of Kuwait, Safat 13060, P.O. Box 5969, Kuwait
Abstract
Proton magnetic resonance spectra of nuclear substituted, N-alkylated- and azaphenothiazines with particular reference to structural elucidation has been discussed.