By Alan R. Katritzky
Proven in 1960, Advances in Heterocyclic Chemistry is the definitive serial within the area--one of significant value to natural chemists, polymer chemists, and lots of organic scientists. Written by way of proven experts within the box, the great studies mix descriptive chemistry and mechanistic perception and yield an knowing of ways the chemistry drives the houses.
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Additional info for Advances in Heterocyclic Chemistry, Vol. 70
4. 13C N M R Spectroscopy Conformational analysis of perhydropyrido[l,2-c] [ldlthiazine (20, X = S) and its truns- and cis-4u,7-H-7-ethyl derivatives indicated that truns4~,7-H-7-ethylperhydropyrido[1,2-c] [13lthiazine and the cis-4u,7-H-7-ethyl analog exist exclusively in the trans-fused and the S-inside cis-fused conformation, respectively, containing the ethyl group in the equatorial positions, whereas the parent perhydropyrido[1,2-~][1,3]thiazinein CDC& at 25°C is a ca. 25 :75 mixture of the S-inside cis-fused and truns-fused conformations.
The basic difference between the trans-fused and cis-fused conformations is that in the trans-fused ring conformations (Teq and Tax)the perhydropyrimidine ring is fused onto the tetrahydropyridine 28 ISTVAN HERMECZ N-inside cis-fused trans-f used 11 NZ inversion (59) 11 NZ inversion [Sec. C N-outside cis-fused li N* inversion Me cis-0, Tax I Me SCHEME10 ring, by utilization of the pseudoequatorial and equatorial bonds of the tetrahydropyridine ring, and this increases the strain in the fused system.
Tetraponerine-T8 (113,R = C5Hll) was prepared similarly by using pentylmagnesium bromide (90TL4543). Treatment of 2,4,4-trimethyl-5-phenyl-l-thioxo-3-oxo-2,3,4,6,7,8hexahydro-lH-pyrido[l,2-c]pyrimidinewith Lawesson's reagent gave a 1,3-dithioxo derivative [968(42)117]. Treatment of a 4-thioxo-l,3,4,6,7,1Ibhexahydro-2H-pyrimido[6,1-a]isoquinolin-2-one derivative with Hg( OAc)2 in boiling acetic acid gave the 2,4-dioxo derivative, and with Raney Ni in boiling ethanol yielded the 2-0x0 derivative (69YZ649).