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The title compound, C(20)H(16)N(2)O, has two molecules in the asymmetric unit and the crystal structure shows that the central pyridine ring of each molecule has a flat boat conformation. The terminal C atom in one of the molecules is disordered over two positions, with relative occupancies of 0.594 (14) and 0.398 (14). Intermolecular C-H.N and C-H.pi interactions and pi-pi stacking, along with intramolecular C-H.N and C-H.pi interactions, help to stabilize the structure.

Some fluoroaryl substituted 2‐amino‐3‐cyanopyrroles 2 were synthesized from the reaction between (2‐bromo‐1‐arylalkylidene)propanedinitriles 1 and fluoroaryl substituted aromatic amines under Gewald reaction condition, which on reaction with formamide and formic acid gave 4‐aminopyrrolo[2,3‐d]pyrimidines 3 and pyrrolo[2,3‐d]‐pyrimidin‐4(3H)‐ones 4 respectively. 4‐Chloropyrrolo[2,3‐d]pyrimidines 5 were prepared by chlorination of 4 with phosphorus oxychloride, which on hydrazinolysis provided 4‐hydrazinopyrrolo[2–3‐d]pyrirnidines 6.

Syntheses of several novel 4-chloropyrrolo[2,3-d]pyrimidines (1), 4- hydrazinopyrrolo[2,3-d]pyrimidines (2) and 3-amino-4-iminopyrrolo[2,3-d]pyrimidines (7) and their use in the synthesis of tetrazolo[1,5-c]pyrrolo[3,2-e]pyrimidines (3) and triazolo[1,5-c]pyrrolo[3,2-e]pyrimidines (4) required for biological screening are reported.

Synthesis of the antileukemic agent 4,4'-diacetyl-N,N-diphenylurea bis (guanylhydrazone) (DDUG) is described in detail. The compound was characterized in terms of its and 13C NMR spectra. To determine the importance of structural features to its biological activity, a series of related compounds was synthesized. The aminoguanidine groups in DDUG were replaced with other groups, such as thiosemicarbazone or nitroaminoguanidine. In addition, one or both H atoms of the urea moiety of DDUG were replaced with a methyl group. One urea N was replaced with 0, giving a urethane moiety. The two guanylhydrazone groups in DDUG were separated with one or two methylene groups, and the effects of such separation were investigated in relation to the biological activity of the compound. In contrast to the modifications that we carried out earlier in the phenyl ring, modifications at and around the urea moiety of DDUG caused decreases in the growth-inhibitory activity of the compound against mouse mammary adenocarcinoma (TA3) cells in culture. Preliminary results indicate that at least some antileukemic activity is retained on single N-methylation and on extension of the molecule with one methylene group. Most of the DDUG analogues inhibited DNA polymerase, and the degree of inhibition was less sensitive to structural modification in this system than in cellular test systems or in vivo.