Regular Issue

Vol. 20, No. 8, 1983

23 data found. 1 - 23 listed
Communication | Regular issue | Vol 20, No. 8, 1983, pp. 1481 - 1485
Published online:
DOI: 10.3987/R-1983-08-1481
Reaction of 4-Acetoxy-1,4-benzoxazin-3-one with Amino Acid Derivatives

Takayoshi Ishizaki, Yuichi Hashimoto, Koichi Shudo, and Toshihiko Okamoto

*Faculty of Pharmaceutical Sciences, University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113, Japan


A reaction of 4-acetoxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one (2) with t-butoxycarbonyl-L-tyrosine ethyl ester (Boc-L-Tyr-OEt), t-butoxycarbonyl-L-histidine methyl ester (Boc-L-His-OMe) and t-butoxycarbonyl-L-tryptophan methyl ester (Boc-L-Trp-OMe) was described. The 4 and 6 positions in the benzozaxinone ring were attacked by the amino acids. The reaction with Boc-L-Trp-OMe gave hexahydropyrroloindoles.

PDF (113KB)
Communication | Regular issue | Vol 20, No. 8, 1983, pp. 1487 - 1489
Published online:
DOI: 10.3987/R-1983-08-1487
Surprising Absence of Reactivity towards Borane of a Cyclic Phenylamine in Two Heterocycles 1,3-Dioxa-2-phosphaIII-6-aza-2-R-6-phenyloctane

Apolonioa Murillo, Rosalinda Contreras, Alain Klaébé, and Robert Wolf

*Centro de Investigación y de Estudios Avanzados, Departmento de Química , I.P.N, Apartado 14-740, México, D.F., 07000, Mexico


The title compound was reacted with an excess of BH3·SMe2 and only one BH3 molecule was added. This phenomenon is discussed.

PDF (77KB)
Communication | Regular issue | Vol 20, No. 8, 1983, pp. 1491 - 1494
Published online:
DOI: 10.3987/R-1983-08-1491
Synthesis of New Orally Absorbed Penem Esters, Structurally Related to Thienamycin and Cephamycins

Maurizio Foglio, Carlo Battistini, Franco Zarini, Cosimo Scarafile, and Giovanni Franceschi

*Ricerca&Sviluppo Chimico, Farmitalia Carlo Erba SpA, Via dei Gracchi 35, 20146 Milano, Italy


The synthesis of two new 6α-hydroxyethyl penem esters, with the relevant feature of a carbamoyloxymethyl moiety in position 2, is described.

PDF (85KB)
Communication | Regular issue | Vol 20, No. 8, 1983, pp. 1495 - 1499
Published online:
DOI: 10.3987/R-1983-08-1495
New Condensed Tri- and Tetracyclic 1,2,4-Triazole Ring Systems

Jan Svetlík

*Drug Research Institute, Palárikova 31, 811 04 Bratislava, Slovakia


A facile two step synthesis of 7,8-dihydroimidazo[1,2-e]-1,2,4-triazolo[1,5-a]-1,3,5-triazine and 1,2,4-triazolo[1’,5’:1,2]-1,3,5-triazino [5,6-a]benzimidazole is described. Heterocyclic hydrazines react easily with ethyl N-cyanoformimidate to form 1,2,4-triazole derivatives, which are then cyclized with ortho esters into hitherto unknown polyazaheterocycles.

PDF (132KB)
Communication | Regular issue | Vol 20, No. 8, 1983, pp. 1501 - 1506
Published online:
DOI: 10.3987/R-1983-08-1501
Structure and Conformation of a New Helenanolide, Pulchelloid C

Seiichi Inayama, Kenzo Harimaya, Hitoshi Hori, Takeshi Kawamata, Tamiko Ohkura, Iwao Miura, and Yoichi Iitaka

*Pharmaceutical Institute, School of Medicine, Keio University, Shinanomachi 35, Shinjuku, Tokyo 160-0016, Japan


The stereostructure, conformation and absolute configuration of pulchelloid C, a new minor component, helenanolide isolated from the methanol extract of Gaillardia pulchella, were deduced by combination of chemical and spectroscopic methods as well as X-ray crystallography.

PDF (145KB)
Communication | Regular issue | Vol 20, No. 8, 1983, pp. 1507 - 1510
Published online:
DOI: 10.3987/R-1983-08-1507
Concurrent Formation of Two Isomeric Dipyridazino[4,5-b:4’,5’-e][1,4]thiazines Attended with Occurrence of a Unique Dipyridazino[4,5-b:4’,5’-d]pyrrole

Kenji Kaji, Hiromu Nagashima, Katsushi Yamaguchi, and Hirohisa Oda

*Gifu Pharmaceutical University, 6-1 Mitahora-higashi 5-chome, Gifu 502-8585, Japan


Interaction of 4-amino-5-mercapto-2-methyl-3(2H)-pyridazinone (1) and 4,5-dichloro-2-methyl-3(2H)-pyridazinone (3) in a basic medium, followed by benzylation, yielded concurrently 10-benzyl-2,7-dimethyl-dipyridazino[4,5-b:4’,5’-e][1,4]thiazine-1,6(2H,7H)-dione (I) and the 2,8-dimethyl-1,9-dione isomer (II). An analogous result leading to a mixture of products, (I) and the alternative 3,7-dimethyl-4,6-dione isomer (III), was also observed in the case of reaction between the 4,5-substituents of counterpart of 1, (2) and (3). Under somewhat more vigorous condition, the condensation reaction of either combination of the reactants added a consecutive formation of a unique 9-benzyl-2,6-dimethyldipyridazino(4,5-b: 4’, 5’-d]pyrrole-1,5(2H,6H)-dione (IV) to that of the mixtures of the respective dipyridazino[1,4]thiazine products (I+II or I+III).

PDF (92KB)
Communication | Regular issue | Vol 20, No. 8, 1983, pp. 1511 - 1517
Published online:
DOI: 10.3987/R-1983-08-1511
Norisohaplophytine and Haplocidiphytine — New Bisindole Alkaloids from Haplophyton cimicidum (Apocynaceae)

Akinbo A. Adesomoju, M. V. Lakshmikantham, and M. P. Cava

*Department of Chemistry, University of Pennsylvania, 231 South 34th Street Philadelphia, PA 19104-6323, U.S.A.


Norisohaplophytine and haplocidiphytine, two new bisindole alkaloids from Haplophyton cimicidum (Apocynaceae) have been assigned the aspidosperma-canthinone structures 1 and 2 respectively.

PDF (132KB)
Communication | Regular issue | Vol 20, No. 8, 1983, pp. 1519 - 1524
Published online:
DOI: 10.3987/R-1983-08-1519
Investigations on Intramolecular Cycloaddition Reactions of Photochemically Generated Carbonyl Ylides

Jürgen Brokatzky-Geiger and Wolfgang Eberbach

*Institut für Organische Chemie und Biochemie, Albert-Ludwigs-Universität Freiburg, Albertstrasse 21, D-7800, Germany


Upon photoexcitation of appropriately substituted oxiranes ring opening leads to carbonyl ylides which undergo intramolecular cycloaddition reactions affording annelated and/or bridged tetrahydrofurans.

PDF (136KB)
Communication | Regular issue | Vol 20, No. 8, 1983, pp. 1525 - 1529
Published online:
DOI: 10.3987/R-1983-08-1525
Syntheses and Cycloadditions of 1,2-Aromatic Ring-fuseed 3-Cyanoindolizines

Kiyoshi Matsumoto, Takane Uchida, Takazumi Sugi, and Takako Kobayashi

*College of Liberal Arts and Science, Kyoto University, Yoshida, Sakyou-ku, Kyoto 606-8501, Japan


The syntheses and 1,3-dipolar and Michael type cycloaddition reactions of 1,2-aromatic ring-fused 3-cyanoindolizines such as benzo[c]pyrrolo[1,2-a]pyridines, 1,3-diphenylthieno[3’,4’:3,4]pyrrolo[1,2-a]pyridines, and 1,4-diphenylpyrido[1’,2’:1, 2]pyrrolo[3,4-d]pyridazines are described.

PDF (97KB)
Communication | Regular issue | Vol 20, No. 8, 1983, pp. 1531 - 1533
Published online:
DOI: 10.3987/R-1983-08-1531
A New Sulfonating Agent on Hetero Atoms

Masayuki Shibuya, Yoshikazu Jinbo, and Seiju Kubota

*Faculty of Pharmaceutical Sciences, University of Tokushima, Sho-machi 1, Tokushima 770-8505, Japan


The novel amidine-N-sulfonic acid (2) was prepared from 3,3,6,9,9-pentamethyl-2,10-diazabicyclo[4.4.0]-1-decene (1) and chlorosulfonic acid. Reaction of 2 with the azetidinone (4) and different hydroxy compounds under rather mild conditions yielded corresponding N- and O-sulfonic acid PDBD salts, which could be purified by the usual column chromatography on silica gel and/or recrystallization.

PDF (73KB)
Communication | Regular issue | Vol 20, No. 8, 1983, pp. 1535 - 1539
Published online:
DOI: 10.3987/R-1983-08-1535
The Pyrolysis and Photolysis of the Protopine Type Alkaloid N-Oxides. The Synthesis of the Secoberbines and Benzo[c]phenanthridines

Kinuko Iwasa and Narao Takao

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


The pyrolysis of the N-oxides of the protopine-type alkaloids afforded three products, one of which was converted to the naturally occurring secoberbines. The photolysis of the N-oxides of the protopines supplied the benzo[c]phenanthridines as well as the one of the pyrolysis products.

PDF (119KB)
Communication | Regular issue | Vol 20, No. 8, 1983, pp. 1541 - 1544
Published online:
DOI: 10.3987/R-1983-08-1541
Influence of Heteroaromatic Amines to Knoevenagel Condensation

Hiroshi Yamanaka, Masaaki Yokoyama, Takao Sakamoto, Takayuki Shiraishi, Mataichi Sagi, and Michinao Mizugaki

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


In the Knoevenagel condensation of hexanal and malonic acid, the ratio of α,β- and β,γ-unsaturated acids was remarkably affected by the nature of tertiary amines used as a catalyst. That is, the condensation in pyridine or isoquinoline gave 2-octenoic acid selectively, whereas the condensation in 2-methylpyridine, 2,6-dimethylpyridine, or quinoline gave 3-octenoic acid as a main product.

PDF (88KB)
Communication | Regular issue | Vol 20, No. 8, 1983, pp. 1545 - 1547
Published online:
DOI: 10.3987/R-1983-08-1545
The Reaction of 2-Substituted Quinoline 1-Oxides with Dimethyl Acetylenedicarboxylate: Formation of 1-Benzazepine Derivatives

Yasuhisa Ishiguro, Kazuhisa Funakoshi, Seitaro Saeki, Masatomo Hamana, Ikuhiko Ueda, and Shigeaki Kawano

*Faculty of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka 812-8582, Japan


The 1,3-dipolar cycloaddition of 2-phenylquinoline 1-oxide (1) and quinaldine 1-oxide (3) with dimethyl acetylenedicarboxylate gives ring expanded products, 2-phenyl- (2) and 2-methyl-3H-3-methoxalyl-3-methoxycarbonyl-1-benzazepines (5), respectively. The reaction of quinaldonitrile 1-oxide (4) yields 1H-2-cyano-3-methoxycarbonyl-1-benzazepine (6) accompanied by further demethoxalylation.

PDF (69KB)
Report | Regular issue | Vol 20, No. 8, 1983, pp. 1549 - 1558
Published online:
DOI: 10.3987/R-1983-08-1549
A Novel One Pot Synthesis of 7,9-Disubstituted 5H-Thiazolo[2,3-b]quinazoline-3,5 [2H]-diones

Munnu Ram Chaurasia and Ajay Kumar Sharma

*Department of Chemistry, D. A. V. (P. G.) College, Dehra Dun, India


Various 7,9-disubstituted 5H-thiazolo[2,3-b]quinazoline-3,5(2H)-diones and 7,9-disubstituted 2-benzylidene-5H-thiazolo[2,3-b]quinazoline-3,5(2H)-diones have been synthesized and screened for various biological activities. Some of the compounds checked fungal growth and also showed significant antibacterial activity.

PDF (200KB)
Report | Regular issue | Vol 20, No. 8, 1983, pp. 1559 - 1562
Published online:
DOI: 10.3987/R-1983-08-1559
Intramolecular Cyclization Reaction of Some 2-Alkenylphenols with Tl(III) Nitrate

Maria Luigia Forcellese, Carlo Alfonsi, Settimia Calvitti, and Enrico Mincione

*del C. N. R., c/o Istituto do Chimica Organica, Università degli Studi di Roma “La Sapienza”, Piazzale Aldo Moro 2 - 00185 Roma, Italy


Some 2-allylphenols give an intramolecular cyclization by reaction with Tl(III) nitrate (TTN) leading to 2-substituted 2,3-dihydrobenzofurans; 2-substituted 2,3-dihydrobenzopyran is obtained from 2-(3-butenyl)phenol with the same reagent.

PDF (115KB)
Report | Regular issue | Vol 20, No. 8, 1983, pp. 1563 - 1566
Published online:
DOI: 10.3987/R-1983-08-1563
Access to a Chirally Substituted Furan. Synthesis of 5-(D-Glycero-1,2-dihydroxyethyl)-2-furaldehyde from a Natural Heptulose

Catherine Fayet and Jacques Gelas

*Laboratoire de Chomie Organique 2, Ecole Nationale Supérieure de Chimie de Clermont-Ferrand, Université de Clermont II, B. P. 45, 63170 Aubière, France


A simple preparative one-step access to a chiral furan [5-(1’,2’(R)-dihydroxyethyl)-2-furaldehyde] from a natural sugar (sedoheptulosan) is described.

PDF (90KB)
Report | Regular issue | Vol 20, No. 8, 1983, pp. 1567 - 1576
Published online:
DOI: 10.3987/R-1983-08-1567
Synthesis of 9-Hexadecen-5-olides; Hypothetical Intermediates in the Biosynthesis of Brefeldin A

Tomihisa Ohta, Masayuki Sunagawa, Kazuko Nishimaki, and Shigeo Nozoe

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


Four types of lactones 1-4 which might be biosynthetic intermediates of brefeldin A have been synthesized. In the course of their synthesis, it was found that coupling of a hydroxy phosphonium salt and a carbomethoxy-aldehyde gave a macrocyclic lactone in onepot probably by a sequential reaction in which intramolecular Wittig condensation followed transesterification.

PDF (284KB)
Report | Regular issue | Vol 20, No. 8, 1983, pp. 1577 - 1580
Published online:
DOI: 10.3987/R-1983-08-1577
Studies on the Syntheses of Heterocyclic Compounds and Natural Products. Part 1007. Synthetic Studies on Cephalosporin Derivatives: An Efrfective Amide Formation Reaction

Tetsuji Kametani, Hiroyasu Sekine, and Toshio Honda

*Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, Japan


An effective amide formation reaction at the C7-position of 7-aminocephalosporanic acid benzhydryl ester has been achieved by the adoption of Mukaiyama’s procedure with a slight modification.

PDF (108KB)
Report | Regular issue | Vol 20, No. 8, 1983, pp. 1581 - 1585
Published online:
DOI: 10.3987/R-1983-08-1581
Synthesis of Some 1H- or 2H,4H-Benzo[4,5]cyclohepta[1,2-c]pyrazol-4-one Derivatives

Christian Deshayes, Michel Chabannet, and Suzanne Gelin

*Département de Biochimie, Laboratoire de Chimie Organique, Institut National des Sciences Appliquées, 20 Avenue Albert Einstein 69621 Villeurbanne Cedex, France


Synthesis of some 1H- or -2H,4H-benzo[4,5]cyclohepta[1,2-c]pyrazol-4-one derivatives from 4-ethoxycarbonyl-1-substituted-5 or 3-styrylpyrazoles is described.

PDF (117KB)
Report | Regular issue | Vol 20, No. 8, 1983, pp. 1587 - 1590
Published online:
DOI: 10.3987/R-1983-08-1587
Selective Ether-Cleavage of Thiocolchicoside and Thiocolchine: Characterization of 3- and 2-Demethylthiocolchicine and Catecholic Congeners

Padam N. Sharma and Arnold Brossi

*Medical Chemistry Section, Laboratory of Chemistry, NIDDK, National Institute of Health, Bethesda, MD 20892, U.S.A.


Selective ether cleavage in the thiocolchicine series took a similar course as observed in the colchicine series. Thiocolchicoside (2) afforded with phosphoric acid, the known 3-demethylthiocolchicine (6), and thiocolchicine (1) gave with conc. sulfuric acid at 70 °C, a mixture of the 2-demethylthiocolchicine (3) and the catechols 4 and 5.

PDF (102KB)
Review | Regular issue | Vol 20, No. 8, 1983, pp. 1591 - 1614
Published online:
DOI: 10.3987/R-1983-08-1591
Heterocyclic Amidines and Hydroxyamidines as Synthons for Bi- and Polycyclic Heterocycles

Miha Tisler

*Department of Chemistry, E. Kardelj University, Murnikova 6, 61000 Ljubljana, Slovenia


This review summarizes the synthetic utility of heterocyclic amidines, N-hydroxyamidines and their derivatives. From these precursors a new heterocyclic ring can be formed, the cyclization involving participation of either a ring nitrogen atom or an ortho functional group.

PDF (381KB)
Review | Regular issue | Vol 20, No. 8, 1983, pp. 1615 - 1640
Published online:
DOI: 10.3987/R-1983-08-1615
Recent Developments in the Chemistry of Ylidene Azolones

Hamed A. Daboun and Sadek E. Abdou

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


The recent developments in the chemistry of ylidene azolones are reported and the literature data were critically discussed.

PDF (450KB)
Review | Regular issue | Vol 20, No. 8, 1983, pp. 1641 - 1653
Published online:
DOI: 10.3987/R-1983-08-1641
The Role of Lone Pair Interactions in the Chemistry of Monosaccharides. The Selective Esterification of 4,6-O-Benzylidene-Hexopyranosides

Vernon G. S. Box

*Department of Chemistry, Mona Campus, University of the West Indies, Mona, Kingston 7, Jamaica


Mechanistic proposals are presented which seek to describe the course of the esterification of a 4,6-O-benzylidene-hexopyranoside by an acid chloride or an acid anhydride. These two proposals are then elaborated into a rationalisation of the selectivity observed in the esterification of the hydroxyl groups of some 4,6-O-benzylidene-hexopyranosides. Central to the rationalisations are the roles of the β- and γ-effects1,2 which determine the relative energies of the lone pair bearing orbitals of the oxygen atoms of the reacting molecules.

PDF (339KB)
23 data found. 1 - 23 listed