Abstract
A convenient synthesis of psoralen derivatives, viz., 7H-furo [3.2-g] [1] benzopyran-7-one (psoralen), 5-methyl-7H-furo [3.2-g] [1] benzopyran-7-one(4-methyl-psoralen) and 5-phenyl-7H-furo [3.2-g] [1] benzopyran-7-one-(4-phenyl-psoralen) by blocking the 8-position of the starting compounds with iodine, subsequentClaisen migration followed by cyclisation is described
Zusammenfassung
Zur Synthese der Titelverbindungen wird die 8-Position des als Ausgangsmaterial dienenden 7-Hydroxy-benzopyranons mit Jod blockiert, dann erfolgt Allylierung und nach einerClaisen-Wanderung die Cyclisierung.
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F. M. Dean, Naturally occurring oxygen ring compounds, p. 198. London: Butterworths. 1963.
T. O. Soine, J. Pharm. Sci.53, 231 (1964).
E. Späth, B. L. Manjunath, M. Pailer, andH. S. Jois, Ber. dtsch. chem. Ges.69, 1087 (1936).
R. T. Foster, A. Robertson, andA. Bushra, J. Chem. Soc.,1948, 2254.
E. C. Horning andD. B. Reisner, J. Amer. Chem. Soc.70, 3619 (1948);72, 1514 (1950).
T. R. Seshadri andM. S. Sood, Indian J. Chem.1, 291 (1963).
D. K. Chatterjee andK. Sen, Sci. Cult.33, 528 (1967).
L. R. Warden, K. D. Kaufman, J. A. Weis, andT. K. Schaaf, J. Org. Chem.34, 2311 (1969).
N. H. Pardanani andK. N. Trivedi, Aust. J. Chem.25, 1537 (1972).
A. Roy, A. D. Gupta andK. Sen, Indian J. Chem.12, 564 (1974).
K. R. Shah andK. N. Trivedi, Aust. J. Chem.27, 1971 (1974).
B. Krisnaswamy andT. R. Seshadri, Proc. Ind. Acad. Sci.A 13, 43 (1941).
F. M. Dean, Naturally occurring coumarins. Fortsch. Chem. Org. Naturstoffe9, 225 (1957).
W. Bridge, A. J. Crocker, T. Cubin, andA. Robertson, J. Chem. Soc.1937, 1533.
H. Pechmann andG. Duisberg, Ber. dtsch. chem. Ges.16, 2122 (1883).
F. W. Canten, F. H. Curd, andA. Robertson, J. Chem. Soc.1931, 1262.
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Ahluwalin, V.K., Prakash, C. & Bala, S. A convenient synthesis of psoralen derivatives: Psoralen, 4-methyl-psoralen and 4-phenyl-psoralen. Monatshefte für Chemie 111, 877–882 (1980). https://doi.org/10.1007/BF00899252
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DOI: https://doi.org/10.1007/BF00899252