By Alan R. Katritzky
Tested in 1960, Advances in Heterocyclic Chemistry is the definitive serial within the area--one of serious significance to natural chemists, polymer chemists, and plenty of organic scientists. Written through verified specialists within the box, the excellent experiences mix descriptive chemistry and mechanistic perception and yield an figuring out of the way the chemistry drives the homes.
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Extra info for Advances in Heterocyclic Chemistry, Vol. 70
Treatment of 9,10-dimethoxy-6,7-dihydro-2H-pyrimido[6,l-u]isoquinolin-2-ones with POC13 gave 2-chloro-6,7-dihydropyrido[6,l-u]isoquinolinium chlorides, which were subsequently reacted with an amine or hydrazide to give 2-(substituted amino)-6,7-dihydropyrimido[6,l-a]isoquinolinium chlorides (82KGS1095). (Earlier the products were described as 4-chloro-2-0x0derivatives [77SAP77/06706; 78GEP27200851). The chlorine atom in 2-chloro6,7-dihydro-4H-pyrimido[6,1-a]isoquinolin-4-ones was substituted with amines [80GEP2847693, 80INIP147624; 81FRP2470130; 84EUP124893, 84USP4482556; 86HCA1671; 89H(29)1929] or with sodium butoxide and phenoxide (84JMC1470), or was hydrolyzed with water [89H(29)1929].
Reactivity of Ring Carbon Atoms Treatment of 4-phenyl-2,3-dihydro-lH-pyrido[l,2-c]pyrimidine-1,3dione with POC13 in the presence of N,N-dimethylaniline gave 3-chloro4-phenyl-lH-pyrido[1,2-c]pyrimidin-l-one. The 3-chloro atom could be substituted by amino and alkoxy groups. Treatment of the 3-chloro derivative with thiourea afforded 4-phenyl-3-thioxo-2,3-dihydro-lH-pyrido[l,2clpyrimidin-l-one (57HCA1319). Treatment of 9,10-dimethoxy-6,7-dihydro-2H-pyrimido[6,l-u]isoquinolin-2-ones with POC13 gave 2-chloro-6,7-dihydropyrido[6,l-u]isoquinolinium chlorides, which were subsequently reacted with an amine or hydrazide to give 2-(substituted amino)-6,7-dihydropyrimido[6,l-a]isoquinolinium chlorides (82KGS1095).
In the latter case, the amino group was acylated with trifluoroacetyl anhydride. 2 equiv of AlBN toluene I 8OoC R = Pr, CHZPh, R' =: H, C(S)Op-TOlyl H (138) The hydroxy group in 137 (R'= H) was acylated with O-p-tolyl chlorothionoformate (96JMC1872). The ester group of 138 (R2 = Me) was hydrolyzed under basic conditions, and the carboxyl group was esterified with benzyl alcohol to give 138 (R2 = CH2Ph). The 6-thionoformate group of 137 (R' = C(S)O-p-Tolyl) was reduced to give 6-unsubstituted bicycles 138 (96JMC1872).
Advances in Heterocyclic Chemistry, Vol. 70 by Alan R. Katritzky