One-pot synthesis of carbazoles via tandem C–C cross-coupling and reductive amination

We have developed a highly efficient synthetic route to carbazoles that employs sequential C–C/C–N bond formation via Suzuki cross-coupling and Cadogan cyclization. The developed method is compatible with electron neutral, rich or deficient substrates. The synthetic utility of this method was demonstrated by the concise syntheses of four natural products.

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Ligand-Controlled Chemoselective One-Pot Synthesis of Dibenzothiazepinones and Dibenzoxazepinones via Twice Copper-Catalyzed Cross-Coupling

Synlett ◽

10.1055/s-0036-1558959 ◽

2017 ◽

Vol 28 (10) ◽

pp. 1201-1208 ◽

Cited By ~ 3

Author(s):

Lanting Xu ◽

Xianhua Pan ◽

Yanyu Chen ◽

Qiujun Peng ◽

Rong Zhang ◽

...

Keyword(s):

Organic Synthesis ◽

Psychotropic Drug ◽

Cross Coupling ◽

One Pot ◽

Highly Efficient ◽

Rapid Access ◽

One Pot Synthesis

A highly efficient and generally applicable protocol, starting from 2-bromobenzamides and 2-bromo(thio)phenols via twice copper-catalyzed couplings to afford dibenzothiazepines and dibenzoxazepinones has been developed. High levels of yield and chemoselectivity are achieved in a single-pot reaction by using an appropriate ligand. Moreover, this facile methodology allows rapid access to a variety of bioactive compounds and known psychotropic drug, which should broaden its application in organic synthesis.

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ChemInform Abstract: One-Pot Synthesis of Carbazoles via Tandem C-C Cross-Coupling and Reductive Amination.

ChemInform ◽

10.1002/chin.201617131 ◽

2016 ◽

Vol 47 (17) ◽

Author(s):

Deuk-Young Goo ◽

Sang Kook Woo

Keyword(s):

Reductive Amination ◽

Cross Coupling ◽

One Pot ◽

One Pot Synthesis

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An Efficient Synthesis of New 7-Trifluoromethyl-2,5-disubstituted Pyrazolo[1,5-a]pyrimidines

Synthesis ◽

10.1055/s-0036-1591752 ◽

2018 ◽

Vol 50 (08) ◽

pp. 1675-1686 ◽

Cited By ~ 7

Author(s):

Mohamed Abarbri ◽

Badr Jismy ◽

Hassan Allouchi ◽

Gérald Guillaumet ◽

Mohamed Akssira

Keyword(s):

Bond Activation ◽

Bond Formation ◽

Building Blocks ◽

Synthetic Route ◽

Efficient Synthesis ◽

One Pot ◽

One Pot Synthesis ◽

Biological Interest ◽

The One

A novel two-step synthesis of trifluoromethylated 3,5-disubstituted pyrazolo[1,5-a]pyrimidines is reported from 3-aminopyrazoles and ethyl 4,4,4-trifluorobut-2-ynoate. The synthetic route begins with the one-pot synthesis of 7-trifluoromethylated pyrazolo[1,5-a]pyrimidin-5-ones by condensation of 3-aminopyrazoles with a fluorinated alkyne. The products obtained are used as building blocks to synthesize directly, with excellent yields via C–O bond activation, a library of new fluorinated 3,5-disubstituted pyrazolo[1,5-a]pyrimidines of biological interest. This operation efficiently allows C–C, C–N and C–S bond formation.

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Correction: One-pot synthesis of carbazoles via tandem C–C cross-coupling and reductive amination

Organic & Biomolecular Chemistry ◽

10.1039/c5ob90196k ◽

2016 ◽

Vol 14 (2) ◽

pp. 786-786

Author(s):

Deuk-Young Goo ◽

Sang Kook Woo

Keyword(s):

Reductive Amination ◽

Cross Coupling ◽

One Pot ◽

One Pot Synthesis

Correction for ‘One-pot synthesis of carbazoles via tandem C–C cross-coupling and reductive amination’ by Deuk-Young Goo, et al., Org. Biomol. Chem., 2016, DOI: 10.1039/c5ob01952d.

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“In Situ” Generated “HCl”: A Highly Efficient Catalyst for One-Pot Synthesis of 1H-Indazolo [1,2-b]phthalazine-1,6,11-triones and 1Hpyrazolo[1,2-b]phthalazine-5,10-diones under Solvent-Free Conditions

Journal of the Mexican Chemical Society ◽

10.29356/jmcs.v58i2.172 ◽

2017 ◽

Vol 58 (2) ◽

Author(s):

Behrooz Maleki ◽

Samaneh Sedigh Ashrafi

Keyword(s):

Phthalic Anhydride ◽

Solvent Free ◽

Synthetic Route ◽

Reaction Conditions ◽

One Pot ◽

Efficient Catalyst ◽

Highly Efficient ◽

One Pot Synthesis ◽

Solvent Free Conditions

The rapid and environmental synthetic route to produce 1H-indazolo[1,2-b] phthalazine-1,6,11-triones and 1H-pyrazolo[1,2-b]phthalazine-5,10-diones derivatives have been developed via multicomponent and one-pot reactions of various aldehydes, cyclic or acyclic 1,3-diketones with: i) phthalhydrazide or ii) phthalic anhydride-hydrazinium hydroxide using wet 2,4,6-trichlorotriazine (TCT) as catalyst under solvent-free conditions. Simple and mild reaction conditions, the use of a cheap catalyst and easy workup and isolation are notable features of this method.

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Deoxygenative C2-heteroarylation of quinoline N-oxides: facile access to α-triazolylquinolines

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.17.42 ◽

2021 ◽

Vol 17 ◽

pp. 485-493

Author(s):

Geetanjali S Sontakke ◽

Rahul K Shukla ◽

Chandra M R Volla

Keyword(s):

Natural Products ◽

Late Stage ◽

Reaction Conditions ◽

One Pot ◽

Highly Efficient ◽

One Pot Synthesis

A metal- and additive-free, highly efficient, step-economical deoxygenative C2-heteroarylation of quinolines and isoquinolines was achieved from readily available N-oxides and N-sulfonyl-1,2,3-triazoles. A variety of α-triazolylquinoline derivatives were synthesized with good regioselectivity and in excellent yields under mild reaction conditions. Further, a gram-scale and one-pot synthesis illustrated the efficacy and simplicity of the developed protocol. The current transformation was also found to be compatible for the late-stage modification of natural products.

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