Zi-Xuan Wang

Divergent Synthesis of Functionalized Quinolines from Aniline and Two Distinct Amino Acids

A practicable quinoline synthesis from aniline and two amino acids was developed for generating a wide range of quinolines with high efficiency and diversity. Thus, it facilitated the creations of pharmaceutical derivatives, photochemical active compounds, and challenging scaffolds. The concept of using two amino acids as heterocyclic precursors has been raised for the first time. Mechanistic studies revealed that I2 enabled decarboxylation, oxidative deamination, and selective reconstruction of new C-N and C-C bonds processes.

Oxidative Trimerization of Amino Acids: Selective Synthesis of 2,3,5-Trisubstituted Pyridines

An oxidative trimerization of three amino acids has been realized to furnish 2,3,5-trisubstuitued pyridines in both cross- and homo-trimerization types. This method is capable of converting simple linear biomass material to heterocycles, which features in the assembly of three amino acid branched chains into one aromatic ring. Molecular iodine triggers the sequential decarboxylation and deamination of amino acids and then promotes the selective formation of new C-N and C-C bonds.

C(sp3)-H Bond Functionalization of Benzo[c]oxepines via C-O bond Cleavage: Formal [3+3] Synthesis of Multi-Substituted Chromans

An efficient base-promoted C(sp3)-H bond functionalization strategy for the synthesis of multisubstituted chromans from the formal [3+3] cycloaddition of benzo[ c]oxepines and electron-rich phenols has been developed. The corresponding 4 H-chromenes can be easily obtained in excellent yields by simple filtration from chromans. Preliminary mechanistic studies indicate that the C-O bond cleavage is the key step for the C(sp3)-H bond functionalization and that this reaction could have occurred through tandem C-O bond cleavage/Michael addition/annulation reactions.

A C–H Oxidation/Two-fold Cyclization Approach to Imidazopyridoindole Scaffold Under Mild Oxidizing Conditions

An expeditious one-step synthesis of the imidazopyridoindole scaffold was achieved through the C-H oxidation/two-fold cyclization reaction of methyl ketone and tryptamine derivatives. Mild oxidizing conditions were employed to realize the efficient oxidation of C(sp3)-H bonds, while suppressing overoxidation of the intermediate and ensuring the cross-trapping of two in situ generated acylimine intermediates.

One-Pot Total Synthesis of Evodiamine and Its Analogues through a Continuous Biscyclization Reaction

The one-pot total synthesis of evodiamine and its analogues is achieved using a three-component reaction. Through continuous biscyclization, various readily available substrates with good functional group tolerance were easily incorporated into biologically active quinazolinocarboline backbones. The use of triethoxymethane as a cosolvent was crucial for this quick and straightforward transformation.

Direct Biomimetic Synthesis of β-Carboline Alkaloids from Two Amino Acids

The increasing importance of enzyme mimics in organic synthesis inspired us to design a novel biomimetic synthesis of β-carboline alkaloids directly from tryptophan and a second amino acid. This novel one-pot protocol utilizes abundant and readily available starting materials and thus presents a green and user-friendly alternative to conventional methods that rely on stepwise synthesis. Driven by molecular iodine and TFA, decarboxylation, deamination, Pictet-Spengler reaction, and oxidation reactions proceeded sequentially, transforming biomass amino acids into value-added alkaloid motifs.

CCDC 1545097: Experimental Crystal Structure Determination

Related Article: Jia-Chen Xiang, Yan Cheng, Zi-Xuan Wang, Jin-Tian Ma, Miao Wang, Bo-Cheng Tang, Yan-Dong Wu, and An-Xin Wu|2017|Org.Lett.|19|2997|doi:10.1021/acs.orglett.7b01232

CCDC 1545079: Experimental Crystal Structure Determination

Related Article: Jia-Chen Xiang, Yan Cheng, Zi-Xuan Wang, Jin-Tian Ma, Miao Wang, Bo-Cheng Tang, Yan-Dong Wu, and An-Xin Wu|2017|Org.Lett.|19|2997|doi:10.1021/acs.orglett.7b01232