Synthesis of fused imidazoles, pyrroles, and indoles with a defined stereocenter α to nitrogen utilizing mitsunobu alkylation followed by palladium-catalyzed cyclization

Journal of Organic Chemistry

Volumn 76, Issue 20, 2011, Pages 8477-8482

  Laha, Joydev K ^a   Cuny, Gregory D ^a  

^a BRIGHAM AND WOMEN S HOSPITAL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYLIC ALCOHOLS; BIOLOGICAL ACTIVITIES; HETEROCYCLES; STEREOCENTERS; SYNTHETIC APPROACH;

ALKYLATION; CARBOXYLATION; CATALYSIS; FUNCTIONAL GROUPS; NITROGEN; PLANTS (BOTANY); STEREOCHEMISTRY;

CYCLIZATION;

1 (1 PHENYLETHYL) 1H PYRROLE 2 CARBONITRILE; 1 (2 BROMOBENZYL) 1H PYRROL N METHYL 2 CARBOXAMIDE; 1 (2 BROMOPHENYLETHYL) 1H PYRROL N METHYL 2 CARBOXAMIDE; 2,2,2 TRICHLORO 1 (1 PHENYLETHYL 1H PYRROLE 2 YL)ETHAN 1 ONE; 2,2,2 TRICHLORO 1 (2 BROMOBENZYL 1H PYRROL 2 YL)ETHAN 1 ONE; 2,2,2 TRICHLORO 1 [1 (2 BROMO)PHENYLETHYL 1H INDOL 3 YL]ETHAN 1 ONE; 2,2,2 TRICHLORO 1 [1 (2 BROMO)PHENYLETHYL 1H PYRROL 2 YL]ETHAN 1 ONE; 2,2,2 TRIFLUORO 1 (1 PHENYLETHYL 1H PYRROLE 2 YL)ETHAN 1 ONE; 5 METHYLPYRROLO[2,1 A]ISOINDOLE N METHYL 3 CARBOXAMIDE; 5H PYRROLO[2,1 C] 2 OXO N METHYL[1,4]BENZODIAZEPINE; 6,7 DIHYDROIMIDAZO[2,1 A][2]BENZAZEPINE; BENZYL ALCOHOL DERIVATIVE; ETHYL 1 (1 PHENYLETHYL) 1H IMIDAZOLE 5 CARBOXYLIC ACID; ETHYL 1 (2 BROMOPHENYL 1 PROPANOL) 1H IMIDAZOLE 5 CARBOXYLIC ACID; ETHYL 1 (2 BROMOPHENYLETHYL) 1H PYRROL 2 CARBOXYLIC ACID; ETHYL 1 [1 (2 BROMO)PHENYLETHYL] 1H IMIDAZOLE 5 CARBOXYLIC ACID; ETHYL 1 [1 (2 BROMO)PHENYLETHYL] 1H INDOLE 3 CARBOXYLIC ACID; ETHYL 4 BROMO 1 (1 PHENYLETHYL) 1H PYRROLE 2 CARBOXYLIC ACID; ETHYL 5 BROMO 1 (1 PHENYLETHYL) 1H PYRROLE 2 CARBOXYLIC ACID; ETHYL 5 METHYLIMIDAZO[2,1 A]ISOINDOLE 3 CARBOXYLIC ACID; ETHYL 5 METHYLIMIDAZO[5,1 A]ISOINDOLE 3 CARBOXYLIC ACID; ETHYL 5 METHYLINDOLO[2,1 A]ISOINDOLE 3 CARBOXYLIC ACID; ETHYL 5 METHYLPYRROLO[2,1 A]ISOINDOLE 3 CARBOXYLIC ACID; ETHYL 5,6 DIHYDROIMIDAZO[2.1 A]ISOQUINOLINE 3 CARBOXYLIC ACID; IMIDAZOLE DERIVATIVE; INDOLE DERIVATIVE; LIGAND; NITROGEN; PALLADIUM; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; MITSUNOBU ALKYLATION; PKA; STEREOCHEMISTRY;

ALKYLATION; ANXIETY; CATALYSIS; CHEMISTRY, PHARMACEUTICAL; CYCLIZATION; ETOMIDATE; GABA AGONISTS; HUMANS; HYPNOTICS AND SEDATIVES; IMIDAZOLES; INDOLES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; NITROGEN; PALLADIUM; PYRROLES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 80054116803     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo201237h     Document Type: Article

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