Two-Step Synthesis of Aza- and Diazaindoles from Chloroamino-<i>N</i>-heterocycles Using Ethoxyvinylborolane

Whelligan, Daniel K.; Thomson, Douglas W.; Taylor, Dawn; Hoelder, Swen

doi:10.1021/jo902143f

Cited by 63 publications

(56 citation statements)

References 37 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Modification or functionalization of existing pyridine structures can be carried out using a variety of strategies. Metal-catalyzed methods range from cross-coupling reactions, such as the Suzuki–Miyaura coupling [ 12 ] and iron-catalyzed cross coupling with Grignard reagents [ 13 ] to direct C–H functionalization [ 14 ]. Minisci reported the addition of carbon-centered radicals to pyridine [ 15 ], although this approach is not always completely selective [ 16 ].…”

Section: Introductionmentioning

confidence: 99%

Regioselective synthesis of pyridines by redox alkylation of pyridine N-oxides with malonates

et al. 2017

View full text Add to dashboard Cite

A regioselective synthesis of pyridines by the addition of malonate anions to pyridine N-oxide derivatives, which have been activated by trifluoromethanesulfonic anhydride, is reported. The reaction selectively affords either 2- or 4-substituted pyridines in good yields.Graphical abstract Electronic supplementary materialThe online version of this article (10.1007/s00706-017-2081-y) contains supplementary material, which is available to authorized users.

show abstract

Section: Introductionmentioning

confidence: 99%

Regioselective synthesis of pyridines by redox alkylation of pyridine N-oxides with malonates

et al. 2017

View full text Add to dashboard Cite

show abstract

“…The Suzuki reaction was also applied to the construction of azaindoles by Swen Hoelder and coworkers [ 25 ]. The authors described an efficient two-step route, starting from chloroamino- N -heterocycles, to prepare a wide range of aza- and diazaindoles, avoiding the use of protecting groups.…”

Section: Metal-catalyzed Cross-coupling Reactionsmentioning

confidence: 99%

Metal-Catalyzed Cross-Coupling Reactions on Azaindole Synthesis and Functionalization

2018

View full text Add to dashboard Cite

Azaindoles are rare in nature but extremely attractive for drug discovery programs. Azaindoles can be obtained by diverse methods, including those involving metal-catalyzed reactions. This important core has been fascinating the scientific community due to their challenging synthesis and relevant bioactivity. This paper highlights the diverse synthetic methodologies developed to date involving metal-catalyzed reaction to attain azaindoles and its functionalization.

show abstract

“…The title compound was previously prepared by Cui et al (2013), and its derivatives were synthesized by Yang & Cheng (2001) and Whelligan et al (2010). We present here the crystal structure of the compound (Fig.…”

Section: Structure Descriptionmentioning

confidence: 99%

4,4,5,5-Tetramethyl-2-[(Z)-1-(3-methylphenoxy)hex-1-en-2-yl]-1,3,2-dioxaborolane

Wang

2016

IUCr Data

View full text Add to dashboard Cite

The title compound was previously prepared by Cui et al. (2013), and its derivatives were synthesized by Yang & Cheng (2001) and Whelligan et al. (2010). We present here the crystal structure of the compound (Fig. 1). In the molecule, the conformation of the dioxaborolane ring is similar to half chair, and the butyl group adopts an extended conformation with a C10-C11-C12-C13 torsion angle = 179.52 (19) . No hydrogen bonding is observed in the crystal. Synthesis and crystallizationTo a solution of 1-(hex-1-yn-1-yloxy)-3-methylbenzene (94 mg, 0.5 mmol) in 2.0 ml of tetrahydrofuran (THF) was added neat 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (HBpin) (71 mg, 0.55 mmol) under nitrogen atmosphere. After stirring at room temperature for 1.5 h, the reaction mixture was concentrated and purified by on silica gel (petroleum ether/EtOAc = 60/1).

show abstract

Two-Step Synthesis of Aza- and Diazaindoles from Chloroamino-N-heterocycles Using Ethoxyvinylborolane

Cited by 63 publications

References 37 publications

Regioselective synthesis of pyridines by redox alkylation of pyridine N-oxides with malonates

Regioselective synthesis of pyridines by redox alkylation of pyridine N-oxides with malonates

Metal-Catalyzed Cross-Coupling Reactions on Azaindole Synthesis and Functionalization

4,4,5,5-Tetramethyl-2-[(Z)-1-(3-methylphenoxy)hex-1-en-2-yl]-1,3,2-dioxaborolane

Contact Info

Product

Resources

About