ISSN:
0941-1216
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Addition of α-Ketoenamines to 2-Acetyl-p-benzoquinoneAddition of 2-morpholino-2-cyclohex-1-en-one 2 to 2-acetyl-quinone 1 yields benzo[c][4 H]chromen-4,7,10-trion 4 which is unstable and rearranges to 5. 4 is converted to 3-(2,5-dihydroxy-phenyl)-2-morpholino-2-cyclohex-1-en-on 3 thermically and to dibenzo[b,d]furan-4-on 7 acid catalyzed. The structure of 7 is secured by independent synthesis. Dibenzo[b,d]furan-4-on 14 is the product of reaction from 2-(p-toluidino)-2-cyclohex-1-en-on 9 and 1 with benzo[c][4 H]chromen-4,7,10-trion 10 as intermediate. By proton catalysis 5-acetyl-6-hydroxy-carbazol-1-on 13 and 4-oxo-cyclohexa[c]isochinolinium hydrochlorid 15 is obtained from 10. 1 H-cyclopenta[d]furan-3-on 17 is formed by addition of 2-(p-toluidino)-2-cyclopent-1-en-on 16 to 1. It is rearranged by proton catalysis to 3-oxo-1 H-cyclopenta[c]isochinolinium salt 18. Reaction of cyclopentan-1,2-dione and 1 yields 3 aH-cyclopenta[c]isochromen-3,6,9-trion 20, rearranging to 1 H-cyclopenta[b]benzo[d]furan-3-on 21. The stereochemistry of adducts is discussed in connection with the course of the reaction, spectroscopical evidence, molecular modelling and calculation of HOMO/LUMO and AO-coefficients.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19933350407
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