By Alan R. Katritzky
Verified in 1960, Advances in Heterocyclic Chemistry is the definitive serial within the area--one of serious value to natural chemists, polymer chemists, and plenty of organic scientists. Written via tested professionals within the box, the great stories mix descriptive chemistry and mechanistic perception and yield an knowing of the way the chemistry drives the houses.
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Additional resources for Advances in Heterocyclic Chemistry, Vol. 70
The N(3)-C(4) double bond of 6,7-dihydro- and 1,6,7,llb-tetrahydro-2H-pyrimido[6,l-u] isoquinolines was saturated by treatment with NaBH4 (81CB61; 84JHC149, 84MI3). Electrochemical reduction of 4-aryl-9,lO-dialkoxy1,6,7,1lb-tetrahydro-2H-pyrimido[6,l-u]isoquinolin-2-ones afforded the 1,3,4,6,7,11b-hexahydro derivatives (87PHA739; 89PHA694). Reduction of 9,10-dimethoxy-2,3,6,7-tetrahydro-4H-pyrimido[6,l-u]isoquinoline-2,4dione with Mg in methanol yielded the 1,2,3,6,7,11b-hexahydroderivative (90JOC5117).
1% to the equilibrium at 25°C. The difference between the trans conformer Taxand the N-inside cis-fused conformer, cis-Zeq,is approximately one guuche-butane interaction (ca. 9 kcal mol-') in favor of Tax,and they should be in an equilibrium ratio of ca. 4: 1 at 25°C. 3 kcal mol-l. On this basis, the equilibrium proportions for 2-methylperhydropyrido[l,2-c]pyrimidine (52, R = Me) are ca. 75% Teq,20% Tax,and 5% cis-&, [76JCS(P2)418]. Thus, perhydropyrido[ 1,2-~]pyrimidines(52) existing in the truns-fused ring conformation (Teq)with an equatorial N(2) alkyl group are expected to have a larger (smaller absolute value) Jgemfor the C(l) methylene group (ca.
4 Hz) and the long-range coupling between 1-He, and 3-He, indicate the predominant presence of trans-fused conformer Taxwith an axial C( -3) alkyl group. 8 Hz for the C(l) methylene protons, which indicate the presence of conformational mixtures containing appreciable amounts of the conformations cis-Z,, and Teq(70T701). 0 Hz for the C(l) methylene protons of 2-methylperhydropyrido[l,2-c]pyrimidin-3-one(55) in CC14, when the nonbridgehead N atom with its lone pair of electrons is incorporated in an amide group, points to the presence of ca.
Advances in Heterocyclic Chemistry, Vol. 70 by Alan R. Katritzky