Regular Issue

Vol. 2, No. 6, 1974

5 data found. 1 - 5 listed
Communication | Regular issue | Vol 2, No. 6, 1974, pp. 649 - 652
Published online:
DOI: 10.3987/R-1974-06-0649
Diazapolycyclic Compounds. IX. Substituted Diazaquinone Adducts with Dimethylenecyclohexane, Dimethylenecyclohexene and nSubstituted Butadienes

Berta López, Manuel Lora-Tamayo,* Pilar Navarro, and José Luis Soto

*Biochemistry Department, Kuwait University, Safat 13060, P.O. Box 5969, Kuwait


Substituted tetracyclic diaza compounds with varying positions of the nitrogen bridge have been synthesized by Diels-Alder reaction of substituted phthalazindiones with 1,2-dimethylenecyclohexane or 1,2- dimethylene-Δ4-cyclohexene and of naphthalazindiones with substituted butadienes in order to obtain compounds referable to tetracyclines of known activity.

PDF (64KB)
Communication | Regular issue | Vol 2, No. 6, 1974, pp. 653 - 657
Published online:
DOI: 10.3987/R-1974-06-0653
The Novel Formation of a Dibenzocyclohepta[b]pyridine by an Abnormal Hofmann Degradation of a Diphenolic Tetrahydroprotoberberinium Salt

Tetsuji Kametani,* Makoto Takemura, Keiichi Takahashi, Mitsuhiro Takeshita, Masataka Ihara, and Keiichiro Fukumoto

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


Heating coreximine methiodide (5) with methanolic potassium hydroxide gave the secoprotoberberine (14) and 5,5a,6,7,8-pentahydro-3,11-dihydroxy-2,10-dimethoxybenz[b,e]-4H-azuleno[3,2,1-ij]isoquinoline (15), but not the methine base (10) usually formed by Hofmann degradation. The possible biogenesis of these two abnormal Hofmann degradation products from protoberberine alkaloids is discussed.

PDF (85KB)
Communication | Regular issue | Vol 2, No. 6, 1974, pp. 659 - 662
Published online:
DOI: 10.3987/R-1974-06-0659
Phenyllithium-Induced Rearrangement of N-Methyltetrahydroberberinium Salts

Yoshikazu Kondo,* Tsunematsu Takemoto, and Kazue Kondo

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


In the presence of phenyllithium or lithium alanate, dl-N-methyltetrahydroberberinium salts underwent rearrangement to N-methyl-7,8-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-spiro-1’-5’,6’-methylenedioxyindane (V). The structure of V has been proven by chemical and spectral means.

PDF (62KB)
Communication | Regular issue | Vol 2, No. 6, 1974, pp. 663 - 668
Published online:
DOI: 10.3987/R-1974-06-0663
Photochemistry of Heterocyclic Compounds. III. Photochemical Reaction of O-Acetylindoxyl

Koji Oe, Masashi Tashiro, and Otohiko Tsuge*

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


Irradiation of O-acetyl indoxyl (I) in benzene solution by a high-pressure mercury lamp afforded indigo (II) and diacetyl (III), and no photo-Fries rearranged products were formed. Upon irradiation of I in the presence of excess benzophenone (IV), however, 2-diphenylmethyleneindolin-3-one (Va) was obtained as a predominant product. The pathways for the formation of II, III, and Va are discussed.

PDF (105KB)
Review | Regular issue | Vol 2, No. 6, 1974, pp. 669 - 743
Published online:
DOI: 10.3987/R-1974-06-0669
Cyclic Hydroxylamines; A Review of Preparative Methods and Properties

Ronald T. Coutts* and Abdel-monaem M. K. El-hawari

*Faculty of Pharmacy and Pharmaceutical Sciences, University of Alberta, Edmonton, Alberta, T6G 2G2, Canada


The preparation of cyclic hydroxylamines by various methods is discussed. These methods include (a) direct N-oxidation of amines, (b) reduction of cyclic nitrones, (c) addition to cyclic nitrones, (d) reductive and non-reductive cyclization reactions, as well as other miscellaneous methods.
The physical and chemical properties of cyclic hydroxylamines which are also discussed are (a) solubility and salt formation, (b) qualitative and quantitative analysis, (c) molecular spectroscopy and mass spectrometry, (d) stability, (e) tautomerism, (f) oxidation, (g) reduction, (h) alkylation reactions, (i) acylation and sulfonation reactions, (j) reactions with nucleophilic reagents, and (k) reactions with electrophilic reagents. Some comments on the biological importance of cyclic hydroxylamines and related compounds are included in an introductory section.

PDF (1.3MB)
5 data found. 1 - 5 listed