Ortho-Directed Metalation of 3-Carboxy-β-carbolines: Use of the SmI2-Cleavable 9-N-(N‘,N‘-Dimethylsulfamoyl) Blocking Group for the Preparation of 9-N-Deprotected 4-Amino Derivatives via Azide Introduction or a Palladium-Catalyzed Cross-Coupling Reaction
- 13 January 1998
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 63 (3) , 872-877
- https://doi.org/10.1021/jo971485l
Abstract
No abstract availableThis publication has 24 references indexed in Scilit:
- Desulfonylation of Amides Using Samarium IodideSynlett, 1997
- Protection of Amines by the Pyridine-2-sulfonyl Group and Its Cleavage under Mild Conditions (SmI2 or Electrolysis)The Journal of Organic Chemistry, 1995
- Benzenoid Ring Functionalization of Indoles and Tryptophols via Combined Directed Ortho Metalation-Cross Coupling MethodologyThe Journal of Organic Chemistry, 1995
- Synthetic Routes to 4-Amino-3-carboxy-.beta.-carboline Derivatives: Incidental Formation of Novel Furo[3,4-c]-.beta.-carbolin-2-ones Displaying High Affinities for the Benzodiazepine ReceptorJournal of Medicinal Chemistry, 1995
- Deprotection of Arenesulfonamides with Samarium iodideThe Journal of Organic Chemistry, 1994
- Preparation and reactions of 1-(tert-butyldimethylsilyl)-3-lithioindole. Regioselective synthesis of 3-substituted indolesThe Journal of Organic Chemistry, 1994
- β‐Carbolines as agonistic or antagonistic benzodiazepine receptor ligands.1. Synthesis of some 5‐, 6‐ and 7‐amino derivatives of 3‐methoxycarbonyl‐β‐carboline (β‐CCM) and of 3‐ethoxycarbonyl‐β‐carboline (β‐CCE)Journal of Heterocyclic Chemistry, 1988
- Regioselective functionalization of pyridinesulfonic acids. Ortho-lithiation of tertiary 2- and 4-pyridinesulfonamidesThe Journal of Organic Chemistry, 1987
- 2,5-Dilithiation of N-protected imidazoles. Syntheses of 2,5-disubstituted derivatives of 1-methoxymethyl-, 1-triphenylmethyl-, and 1-(N,N-dimethylsulphonamido)-imidazoleJournal of the Chemical Society, Perkin Transactions 1, 1984
- Reaction of arylsulfonyl azides with N-methylindoleThe Journal of Organic Chemistry, 1973