LH-<Pyrrolo

A series of 4-(l-piperidinyl)-lH-pyrrolo[2,3-b]pyridines (16), 6-(l-piperidi-nyl)-lH-purines (17) and 4-(l-piperidinyl)-lH-pyrazolo[3,4-d]pyrimidines (18) were reported as AKT inhibitors [28-30]. Compounds 16 and 17 were described as having AKT IC50 <10 pM, whereas compound 18 was described as having AKT IC50 < 50 nM. 

Cyclische Carbonsaure-anhydride bilden mit o-Diamino-arenen N-(2-Amino-phenyl)-dicar-bonsaure-imide. Durch einfaches Erhitzen in Eisessig cyclisieren die N-(2-Amino-phenyl)-ma-leinsaure-imideI zu l-Oxo-lH-[Pg.232]

The stereochemistry of the cycloaddition has been studied through the reaction with methyl fumarate and maleate. The geometry is preserved and trans- and d.v-adducts are obtained. The di-adduct isomerizes rapidly into the frans-adduct on standing at room temperature. Indications of the regiochemistry were obtained from reaction with acrylonitrile which gives 2,3-dihydro-l-cyano-9-methyl-lH-pyrrolo[l,2a]indole exclusively.407,408... 

It is interesting to note that the reaction with maleic anhydride leads exclusively to a carboxylic acid, 2,3-dihydro-9-methyl-lH-pyrrolo[l,2a]indole-2-carboxylic acid, with a regiochemistry different from that observed in the case of acrylonitrile and from that... 

Benchekroun-Mounir, N., Dugat, D., Gramain, J.C., and Husson, H.P. (1993) Stereocontrolled formation of octahydro-lH-pyrrolo[2,3-d]carbazoles by reductive cydization total synthesis of ( )-N-benzylaspidospermidine. Journal of Organic Chemistry, 58, 6457-6465. 

PQQ (methoxatin 4,5-dihydro-4,5-dioxo-lH-pyrrolo [2,3-f] quinoline-2,7, 9-tricarboxylic acid), 2-(dimethylamino) ethanethiol (DMAET), 2-(diethylamino) ethanethiol (DEAET), and pyrrole were purchased from Sigma (St. Louis, MO). Potassium hydrogen phthalate was purchased from Acros (Pittsburgh, PA). Pyrrole was distilled every time immediately before use. All other regents were used without further purification. 

Heterocyclic-lH-pyrrolo[2,3-b]pyridine derivatives, (III), prepared by Matsuoka (3) were effective as selective COX-II inhibitors and used in treating pain and inflammation disorders. 

Preparation of 5-methyl-4-(lH-pyrrolo[2,3-b]pyridin-5-yloxy)-pyrrolo [2,l-f][l,2,4]triazine-6-carboxylic acid ethyl ester... 

Preparation of /G(+)-3-A,-acetyl-2,3-dihydro-7-methyl-lH-pyrrolo[l,2-a] benzimidazole... 

Amino-2,3-dihydro-7-methyl-lH-pyrrolo[l,2-a]benz-imidazole (2.9 mmol) was added to ALTUS 20 CLEC (310 mg) in 104 ml EtOAc, then stirred 30 minutes, and filtered. The solution was washed three times with 10 ml CHC13, then concentrated. The residue was purified by chromatography using silica gel with 3% methyl alcohol in CHC13, then recrystallized from EtOAc/hexane, and the product isolated in 37% yield, mp = 219-220°C. 

Preparation of R-(+)-3-A-trifluoroacetyl-6-bromo-2,3-dihydro-7-methyl-5-nitro-lH-pyrrolo-[l,2-a]benzimidazole... 

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