Summary
Reaction of 9(10H)-acridinone (2) with 3-chloro-3-phenyl-1-propyne under PTC conditions affords 1-methyl-2-phenyl-6H-pyrrolo[3,2,1-de]acridin-6-one (1 b), 10-(2-chloro-1-methyl-2-phenyl-ethenyl)-9(10H)-acridinone (4), 10-(3-phenyl-1-propynyl)-9(10H)-acridinone (7), and 10-(4-methylene-2,3-diphenyl-2-cyclobuteneylidenemethyl)-9(10H)-acridinone (5). The structure of the last compound which crystallizes in the triclinic system with the space group\(P\bar 1\), was confirmed by X-ray diffraction. Under the same conditions 10-(3-phenyl-2-propynyl)-9(10H)-acridinone (3) and 10-(3-phenyl-1-propynyl)-9(10H)-acridinone (6) were obtained from 9(10H)-acridinone (2) and 3-bromo-1-phenyl-1-propyne.
Similar content being viewed by others
Literatur
13. Mitt.: Reisch J., Usifoh C. O., Oluwadiya J. O. (1989) J. Heterocycl. Chem.26: 1495
Teil der Dissertation Salehi-Artimani R. A. (1988) Münster; auszugsweise als Poster, präsentiert bei der Jahrestagung der DPhG (9.–13. September 1987 in Münster); siehe auch: Salehi-Artimani R. A., Reisch J., Henkel G. (1987) Arch. Pharm. (Weinheim)320: 974
Reisch J., Salehi Artimani R. A. (1985) Monatsh. Chem.116: 1099
Seebach D. (1971) In: Houben-Weyl-Müller (eds.) Methoden der Organischen Chemie, 4. Aufl. Thieme, Stuttgart, Bd. IV/4, S. 18 f
Hennion G. F., Nelson K. W. (1957) J. Am. Chem. Soc.79: 2142
Ibers J. A., Hamilton W. C. (1974) International Tables for X-Ray Crystallography, Bd. 4. Kynoch Press, Birmingham
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Reisch, J., Salehi-Artimani, R.A. & Henkel, G. Acetylenchemie, 14. Mitt.: PTC-Umsetzung von 9(10H)-Acridinon mit 3-Chlor-3-phenyl-1-propin und 3-Brom-1-phenyl-1-propin. Monatsh Chem 121, 147–155 (1990). https://doi.org/10.1007/BF00809527
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00809527