Studies on Heterocyclic Analogs of Azulene. VI. Cycloadditions of Styryl-substituted Aza Analogs of Azulene with Dimethyl Acetylenedicarboxylate
- 1 May 1980
- journal article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 53 (5) , 1406-1413
- https://doi.org/10.1246/bcsj.53.1406
Abstract
8-[(E)-Styryl]-1-azaazulenes stereospecifically react with dimethyl acetylenedicarboxylate to form trans-7H-6a-azacyclobuta[j]cyclopent[cd]azulene (3), which undergoes thermal rearrangement into 3-[(E)-styryl]3H-2a-azacyclopent[cd]azulene and 3a,4-dihydro-3H-2a-azadicyclopent[cd, ij]azulene (7), or isomerization into 3H-2a-azacyclopenta[ef]heptalene by silica gel. Compound 7 is oxidized during the course of reaction to yield 11-oxo-2aH-7,10b-methano-2a-azacyclopenta[ab]cycloundecene, compound 3 forming 5a,6-dihydro-3H-2a-azadicyclopenta[ef, kl]heptalene upon reaction with acetylene. The formation of 3 could be accounted for in terms of a symmetry-allowed thermal [_π2_s+_π2_a+_π6_a] cycloadditionKeywords
This publication has 10 references indexed in Scilit:
- 1,5-Dipolar cyclizationsChemical Reviews, 1979
- The pyrrolo[3,4-c]pyrazole system, a new 10.pi.-electron heteropentaleneThe Journal of Organic Chemistry, 1979
- Reactions of Acetylenecarboxylic Esters with Nitrogen-Containing HeterocyclesAdvances in Heterocyclic Chemistry, 1979
- Studies on Heterocyclic Analogues of Azulene. Part 5. Rearrangement of 7H-6a-Azacyclobuta[j]cyclopent[1,2,3-cd]azulene Ring System on Silica GelHETEROCYCLES, 1979
- Neue thermische Cycloadditionen eines Thieno[3,4‐ c ]isothiazols an Alkine und AlkeneEuropean Journal of Inorganic Chemistry, 1979
- Mesomeric betaine derivatives of heteropentalenesTetrahedron, 1977
- Cycloaddition reactions of cyclopropane-containing compounds. VIII. Stereochemical aspects of the cycloaddition of alkenylidenecyclopropanes with 4-phenyl-1,2,4-triazoline-3-5-dione. Evidence in support of a concerted cycloaddition pathwayJournal of the American Chemical Society, 1974
- Mechanisms of Elimination Reactions. IX. The Spontaneous Decomposition of Salts of β-Halo Acids. II. trans-Cinnamic Acid Dibromide1Journal of the American Chemical Society, 1953
- The Stereochemistry and Mechanism of the Transformation of Cinnamic Acid Dibromide to β-Bromostyrene1Journal of the American Chemical Society, 1953
- SOME ALPHA-ALKYLCINNAMIC ACIDS AND THEIR DERIVATIVESJournal of the American Chemical Society, 1932