By Alan R. Katritzky
Validated in 1960, Advances in Heterocyclic Chemistry is the definitive serial within the area--one of significant value to natural chemists, polymer chemists, and plenty of organic scientists. Written through proven experts within the box, the great reports mix descriptive chemistry and mechanistic perception and yield an figuring out of the way the chemistry drives the homes.
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Extra resources for Advances in Heterocyclic Chemistry, Vol. 70
5 h 36% SCHEME14 2. Reactivity of Rings The reaction of 1,3,4,4~,5,10-hexahydro~l,3]thiazino[3,4-b]isoquinolinel-thione and methyl iodide gave l-methylthio-4,4~,5,1O-tetrahydro-3H[1,3]thiazino[3,4-b]isoquinoliniumiodide, which reacted with 5-aminoisoquinoline in pyridine at 40°C to afford l-(5-isoquinolylirnino)-1,3,4,4~,5, l0-hexahydro[l,3]thiazino[3,4-b]isoquinoline(79GEP2848926). Sec. C] PYRIDO[1,2-c][1,3]OXAZINES, -THIAZINES, & -PYRIMIDINES, I1 41 The 4-(substituted imino) moiety of 1,2,4,6,7,11b-hexahydro-2H-[l,3]thiazino[4,3-~]isoquinolineswas substituted with another (substituted imino) group when 9,10-dimethoxy-l-hydroxymethyl-4-(substituted imino)-1,2,4, 6,7,llb-hexahydro-[l,3]thiazino[4,3-a]isoquinolines were reacted with primary amines in boiling ethanol (85GEP3510526).
Ring Transformation 2-Aryl-1,6,7,8,9,9a-hexahydro-4H-quinolizines were obtained when 3aryl-methylperhydropyrido[1,2-c][1,310xazine hydrochlorides were heated in concentrated hydrochloric acid (60BRP856357; 62USP3031454). Ethyl 4,5,6,7,8,8a-hexahydro-3~-quinolizine-l-carboxylate was obtained 1,2-c][1,310xazine-4-carin 82% yield from l-oxo-3-vinylperhydropyrido[ boxylate on the action of DBU in DMSO [88CPB1597; 90H(30)885]. Rearrangement of [1,3]oxazino[3,4-a]quinoline(67, R = H) in the presence of NaOMe in cyclohexane at 65°C produced benzo(c)quinolizine-1,3-dione (99) (71JOC2211).
The O-outside cis conformer, cis-O,,, should be higher in energy than the trans conformer Teqby approximately the value for the cis-truns-quinolizidine, AGO, and should therefore contribute only ca. 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.
Advances in Heterocyclic Chemistry, Vol. 70 by Alan R. Katritzky