Advances in Heterocyclic Chemistry, Vol. 70 by Alan R. Katritzky

By Alan R. Katritzky

Validated 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 by way of tested professionals within the box, the excellent stories mix descriptive chemistry and mechanistic perception and yield an knowing of ways the chemistry drives the homes.

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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). The reaction of 2-cyanomethylperhydropyrimidine with LAH gave the 2-(2-aminoethyl) derivative (69JHC181).

Treatment of 2-benzyl-9chloro-1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinazolin-7-onewith NaN3 in chloroform in the presence of concentrated H2S04 gave 2-benzyl-10chloro-1,2,3,5,6,7-hexahydro-8H-pyrimido[5,6,1-jk][1,4]benzodiazepin-8one (72MI1). 7 . Miscellaneous Cyclocondensation of l-methylthio-4,4~,5,6,7,8-he~ahydro-3H-pyrido [1,2-c]pyrimidine (139)with anthranilic acids (71JMC878; 72USP3631046; 74USP3772230;75USP3868372)or with ethyl 5-amino-3-methylisothiazole4-carboxylate [76IJC(B)391] afforded the tetracyclic derivatives 140 and 141, respectively.

HCl. 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).

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