23543-62-6Relevant articles and documents
Negishi Cross-Coupling Provides Alkylated Tryptophans and Tryptophan Regioisomers
Dachwitz, Steffen,Scharkowski, Bjarne,Sewald, Norbert
supporting information, p. 18043 - 18046 (2021/11/16)
Mild transition-metal catalysed cross-couplings enable direct functionalisation of biocatalytically halogenated tryptophans with alkyl iodides, representing a new alternative for late-stage derivatisations of halogenated aromatic amino acids. Moreover, this strategy enables preparation of (homo)tryptophan regioisomers in a simple two-step synthesis using a Pd-catalysed Negishi cross coupling. This method provides access to non-canonical constitutional surrogates of tryptophan, ready for use in peptide synthesis.
Nickel-Catalyzed Cross-Coupling of Anisoles with Alkyl Grignard Reagents via C-O Bond Cleavage
Tobisu, Mamoru,Takahira, Tsuyoshi,Chatani, Naoto
supporting information, p. 4352 - 4355 (2015/09/15)
Nickel-catalyzed cross-coupling of methoxyarenes with alkyl Grignard reagents, which involves the cleavage of the C(aryl)-OMe bond, has been developed. The use of 1,3-dicyclohexylimidazol-2-ylidene as a ligand allows the introduction of a variety of alkyl groups, including Me, Me3SiCH2, ArCH2, adamantyl, and cyclopropyl. The method can also be used for the alkylative elaboration of complex molecules bearing a C(aryl)-OMe bond.
Palladium-catalyzed synthesis of heterocycle-containing diarylmethanes through suzuki-miyaura cross-coupling
Kuriyama, Masami,Shinozawa, Mina,Hamaguchi, Norihisa,Matsuo, Seira,Onomura, Osamu
, p. 5921 - 5928 (2014/07/08)
The heterocycle-containing diarylmethane synthesis from chloromethyl(hetero)arenes with (hetero)arylboron reagents was attained using the palladium/ether-imidazolium chloride system. This coupling process tolerated a diverse range of heteroaromatic moieties with sufficient catalytic activity to achieve the efficient synthesis of various diheteroarylmethanes in good to excellent yields.
Single-electron transmetalation in organoboron cross-coupling by photoredox/nickel dual catalysis
Tellis, John C.,Primer, David N.,Molander, Gary A.
, p. 433 - 436 (2014/08/05)
The routine application of Csp3-hybridized nucleophiles in cross-coupling reactions remains an unsolved challenge in organic chemistry. The sluggish transmetalation rates observed for the preferred organoboron reagents in such transformations are a consequence of the two-electron mechanism underlying the standard catalytic approach. We describe a mechanistically distinct single-electron transfer-based strategy for the activation of organoboron reagents toward transmetalation that exhibits complementary reactivity patterns. Application of an iridium photoredox catalyst in tandem with a nickel catalyst effects the cross-coupling of potassium alkoxyalkyl- and benzyltrifluoroborates with an array of aryl bromides under exceptionally mild conditions (visible light, ambient temperature, no strong base). The transformation has been extended to the asymmetric and stereoconvergent cross-coupling of a secondary benzyltrifluoroborate.
Tryptamine analogues as 5-ht1-like agonists
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, (2008/06/13)
A compound of structure (I), in which A1 is O, S(O)n in which n is 0, 1 or 2, NR, CH2, or CH(OH); A2 is a bond or CH2 ; or A1 A2 is CH=CH; R is hydrogen or C1-4 alkyl;
5-HT-1D receptor ligands
-
, (2008/06/13)
Described herein are tryptamine analogs that display high binding affinity and selectivity for the 5-HT1Dβ receptor, of the formula: STR1 wherein R 1 is a group selected from aryl-C 1-7 alkyl; aryl-C 2-7 alkoxy; aryl-C 2-7 alkanoyl and aryl-C 1-7 alkanoyloxy, wherein said alkyl, alkoxy, alkanoyl and alkanoyloxy groups are optionally substituted by a C 1-4 alkyl substituent and wherein said aryl group is optionally substituted by one or more substituent selected from hydroxyl, halogen, mercapto, linear or branched C 1-4 alkyl, linear or branched C 1-4 alkoxy, linear or branched C 1-4 alkylthio, thiol substituted C 1-4 alkyl and nitro substituted C 1-4 alkyl;R 2 and R 3 are selected independently from H and C 1-4 alkyl; andR 4 is selected from H, C 1-4 alkyl, aryl and arylC 1-4 alkyl. The compounds are useful as reagents for receptor identification and in receptor-based drug screening programs, and can also be used therapeutically to treat conditions for which administration of a 5-HT1D ligand is indicated, for example in the treatment of migraine.
Binding of 5-Arylalkyloxytryptamines at Human 5-HT1Dβ Serotonin Receptors
Hong, Seoung-Soo,Dukat, Malgorzata,Teitler, Milt,Herrick-Davis, Kathy,McCallum, Kirk,et al.
, p. 690 - 699 (2007/10/03)
Several 5-substituted tryptamine derivatives were prepared and examined for their binding at 5-HT1D serotonin receptors. Initially, a region of bulk tolerance was probed. Subsequently, a series of 5-(arylalkyloxy)tryptamines was prepared. Within a homolog
