ChemInform Abstract: Synthesis of 4‐Hydrazino‐5H‐pyrimido(5,4‐b)indole and Related Compounds.

Abstract

The 3‐amino‐indol‐2‐carboxylate (I) and formamide are condensed to form the pyrimido‐indolone (IIa) which is sulfurized to (IIb).

Tyrosine Kinase Inhibitors. 16. 6,5,6-Tricyclic Benzothieno[3,2-d]pyrimidines and Pyrimido[5,4-b]- and -[4,5-b]indoles as Potent Inhibitors of the Epidermal Growth Factor Receptor Tyrosine Kinase

“…A mixture of 4-chloro-5H-pyrimido [5,4-b]indole hydrochloride 23 (11) (731 mg, 3.6 mmol), dimethyl sulfate (0.41 mL, 4.3 mmol), Cs2-CO3 (3.5 g, 10.7 mmol), activated 3A molecular sieves (2.7 g), and acetone (10 mL) was heated at reflux for 6 h, then stirred at 25 °C for 36 h. The suspension was filtered over Celite and the filtrate was concentrated to a solid that was distributed between CHCl3 and 1% aq NaOH. The organic layer was washed with H2O (2×), dried, and concentrated to a solid that was purified by column chromatography eluting with 0% and then 1% EtOH in CHCl3.…”

“…The pooled product fractions were concentrated to a residue that was crystallized to give 12 (278 mg, 35%): mp 153-154 °C (lit. 23 mp 145-146 °C).…”

“…N-Phenyl-5H-pyrimido [5,4-b]indole-4-amine Hydrochloride (34). Reaction of 4-chloro-5H-pyrimido [5,4-b]indole hydrochloride (11) 23 (240 mg, 1.0 mmol), aniline (0.273 mL, 3 mmol), and EtOH (1 mL) was followed by dilution of the suspension with EtOH (4 mL). The solid was collected, washed with H2O and EtOH, and then recrystallized from DMF/H2O to give 34 ( The lower band was extracted to give 67 (12 mg, 3%) as a yellow solid: mp 193-194 °C; 1 H NMR δ 9.65 (1H, br s, NH), 8.68 (1H, s, H-2), 8.14 (1H, d, J ) 1.9 Hz, H-2′), 7.79-7.76 (2H, m, H-6, H-6′), 7.29-7.23 (3H, m, H-5′, H-4′, H-9), 6.99 (1H, dd, J ) 2.4, 8.8 Hz, H-7), 6.03 (1H, q, J ) 5.1 Hz, NHCH3), 2.73 (3H, d, J ) 4.9 Hz, NHCH3); CIMS m/z (relative intensity) 387 ( 81 Br, MH + , 92), 386 ( 81 Br, M + , 97), 385 ( 79 Br, MH + , 100), 384 ( 79 Br, M + , 77).…”

“…Chemistry 4-Amino-substituted pyrimido [5,4-b]indole analogues were prepared as detailed in Scheme 1. Condensation of 4-chloropyrimido [5,4-b]indole 23 (11) with a variety of aliphatic and aromatic amines to give target compounds 34, 35, and 37-41 listed in Table 1. The preferred conditions were to carry out the reaction in a refluxing lower alcohol (and on occasion DMA) with a catalytic amount of HCl (procedure A).…”

Synthesis of Some Novel N7-tetrazolo[5,1-f]-1,2,4-triazin-8-(7H)-one Compounds as Potential Antimicrobial Agents

“…Various reviews. 12−14 dealing with the synthesis of condensed 1,2.4-triazine moiety plays a vital role in many biological activities including antiviral, 15 antihypertensive, 15,16 blood-platelet aggregation inhibitory, 16,17 analogesic, 18 and antibacterial properties, 19,20 as well as some of new anti-HIV and anticancer agents. 21 In report here high yield synthetic procedures for the preparation of the title compounds and their full characterization data.…”