A Domino Heck Coupling–Cyclization–Dehydrogenative Strategy for the One-Pot Synthesis of Quinolines

Synthesis ◽  
2021 ◽  
Author(s):  
Santanu Ghora ◽  
Chinnabattigalla Sreenivasulu ◽  
Gedu Satyanarayana
Keyword(s):  
Functional Group ◽  
Exchange Process ◽  
Palladium Catalysis ◽  
Allylic Alcohols ◽  
Heck Coupling ◽  
One Pot ◽  
Synthetic Process ◽  
Intramolecular Condensation ◽  
The One

AbstractAn efficient, one-pot, domino synthesis of quinolines via the coupling of iodoanilines with allylic alcohols facilitated by palladium catalysis is described. The overall synthetic process involves an intermolecular Heck coupling between 2-iodoanilines and allylic alcohols, intramolecular condensation of in situ generated ketones with an internal amine functional group, and a dehydrogenation sequence. Notably, this protocol occurs in water as a green solvent. Significantly, the method exhibits broad substrate scope and is applied for the synthesis of deuterated quinolines through a deuterium-exchange process.

scholarly journals NIR responsive tumor vaccine in situ for photothermal ablation and chemotherapy to trigger robust antitumor immune responses

2021 ◽  
Vol 19 (1) ◽  
Author(s):  
Lirong Zhang ◽  
Jingjing Zhang ◽  
Lixia Xu ◽  
Zijian Zhuang ◽  
Jingjin Liu ◽  
...  
Keyword(s):  
Immune Responses ◽  
Tumor Vaccine ◽  
Oxidative Polymerization ◽  
Delivery Mode ◽  
Tumor Treatment ◽  
One Pot ◽  
Photothermal Ablation ◽  
Prolonged Retention ◽  
The One

Abstract Background Therapeutic tumor vaccine (TTV) that induces tumor-specific immunity has enormous potentials in tumor treatment, but high heterogeneity and poor immunogenicity of tumor seriously impair its clinical efficacy. Herein, a novel NIR responsive tumor vaccine in situ (HA-PDA@IQ/DOX HG) was prepared by integrating hyaluronic acid functionalized polydopamine nanoparticles (HA-PDA NPs) with immune adjuvants (Imiquimod, IQ) and doxorubicin (DOX) into thermal-sensitive hydrogel. Results HA-PDA@IQ NPs with high photothermal conversion efficiency (41.2%) and T1-relaxation efficiency were using HA as stabilizer by the one-pot oxidative polymerization. Then, HA-PDA@IQ loaded DOX via π-π stacking and mixed with thermal-sensitive hydrogel to form the HA-PDA@IQ/DOX HG. The hydrogel-confined delivery mode endowed HA-PDA@IQ/DOX NPs with multiple photothermal ablation performance once injection upon NIR irradiation due to the prolonged retention in tumor site. More importantly, this mode enabled HA-PDA@IQ/DOX NPs to promote the DC maturation, memory T cells in lymphatic node as well as cytotoxic T lymphocytes in spleen. Conclusion Taken together, the HA-PDA@IQ/DOX HG could be served as a theranostic tumor vaccine for complete photothermal ablation to trigger robust antitumor immune responses.

scholarly journals One-Pot Synthesis of Novel Multisubstituted 1-Alkoxyindoles

Molecules ◽  
2021 ◽  
Vol 26 (5) ◽  
pp. 1466
Author(s):  
Ye Eun Kim ◽  
Hyunsung Cho ◽  
Yoo Jin Lim ◽  
Chorong Kim ◽  
Sang Hyup Lee
Keyword(s):  
Alkyl Halide ◽  
The Novel ◽  
Reaction Conditions ◽  
One Pot ◽  
One Pot Synthesis ◽  
Consecutive Reactions ◽  
Intramolecular Condensation ◽  
Synthetic Sequence ◽  
Novel Target

Studies on a one-pot synthesis of novel multisubstituted 1-alkoxyindoles 1 and their mechanistic investigations are presented. The synthesis of 1 was successfully achieved through consecutive four step reactions from substrates 2. The substrates 2, prepared through a two-step synthetic sequence, underwent three consecutive reactions of nitro reduction, intramolecular condensation, and nucleophilic 1,5-addition to provide the intermediates, 1-hydroxyindoles 8, which then were alkylated in situ with alkyl halide to afford the novel target products 1. We optimized the reaction conditions for 1 focusing on the alkylation step, along with the consideration of formation of intermediates 8. The optimized condition was SnCl2·2H2O (3.3 eq) and alcohols (R1OH, 2.0 eq) for 1–2 h at 40 °C and then, base (10 eq) and alkyl halides (R2Y, 2.0 eq) for 1–4 h at 25–50 °C. Notably, all four step reactions were performed in one-pot to give 1 in good to modest yields. Furthermore, the mechanistic aspects were also discussed regarding the reaction pathways and the formation of side products. The significance lies in development of efficient one-pot reactions and in generation of new 1-alkoxyindoles.

Facile synthesis of chiral indolines through asymmetric hydrogenation of in situ generated indoles

2018 ◽  
Vol 5 (19) ◽  
pp. 2805-2809 ◽  
Author(s):  
Chang-Bin Yu ◽  
Jie Wang ◽  
Yong-Gui Zhou
Keyword(s):  
Asymmetric Hydrogenation ◽  
Hydrogenation Process ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Facile Synthesis ◽  
One Pot ◽  
Brönsted Acid ◽  
Palladium Catalyzed ◽  
Intramolecular Condensation

A concise synthesis of chiral indolines has been developed through intramolecular condensation, deprotection and palladium-catalyzed asymmetric hydrogenation in a one-pot process with up to 96% ee. A strong Brønsted acid played an important role in both the formation of indoles and asymmetric hydrogenation process.

Direct Propargylation of ortho-Quinone Methides with Alkynyl Zinc Reagents: An Application to the One-Pot Synthesis of 2,3-Disubstituted Benzofurans

Synlett ◽  
2020 ◽  
Vol 31 (08) ◽  
pp. 818-822
Author(s):  
Hongjun Ren ◽  
Manman Sun ◽  
Jinyu Song ◽  
Lei Wang ◽  
Wenguang Yin ◽  
...  
Keyword(s):  
Transition Metal ◽  
Functional Group ◽  
Quinone Methides ◽  
One Pot ◽  
Metal Free ◽  
Efficient Strategy ◽  
One Pot Synthesis ◽  
Subsequent Cyclization ◽  
The One

A transition-metal-free propargylation of ortho-quinone methides (o-QMs) with alkynyl zinc reagents was achieved. A conjugate alkynylation of an o-QM and subsequent cyclization sequence in the presence of KOt-Bu for the synthesis of 2,3-disubstituted benzofurans in one pot was developed. This efficient strategy exhibits good functional-group compatibility and gives moderate to good yields. The present reaction might serve as an attractive method for the synthesis of polysubstituted benzofurans.

scholarly journals A One-Pot Synthesis and Characterization of Antibacterial Silver Nanoparticle–Cellulose Film

Polymers ◽  
2020 ◽  
Vol 12 (2) ◽  
pp. 440 ◽  
Author(s):  
Qi-Yuan Chen ◽  
Sheng-Ling Xiao ◽  
Sheldon Q. Shi ◽  
Li-Ping Cai
Keyword(s):  
Composite Film ◽  
Food Packaging ◽  
Antibacterial Activities ◽  
Light Transmittance ◽  
Ag Nps ◽  
One Pot ◽  
One Pot Synthesis ◽  
The One

Using N,N-dimethylacetamide (DMAc) as a reducing agent in the presence of PVP-K30, the stable silver nanoparticles (Ag-NPs) solution was prepared by a convenient method for the in situ reduction of silver nitrate. The cellulose–Ag-NPs composite film (CANF) was cast in the same container using lithium chloride (LiCl) giving the Ag-NPs-PVP/DMAc solution cellulose solubility as well as γ-mercaptopropyltrimethoxysilane (MPTS) to couple Ag-NPs and cellulose. The results showed that the Ag-NPs were uniformly dispersed in solution, and the solution had strong antibacterial activities. It was found that the one-pot synthesis allowed the growth of and cross-linking with cellulose processes of Ag-NPs conducted simultaneously. Approximately 61% of Ag-NPs was successfully loaded in CANF, and Ag-NPs were uniformly dispersed in the surface and internal of the composite film. The composite film exhibited good tensile properties (tensile strength could reach up to 86.4 MPa), transparency (light transmittance exceeds 70%), thermal stability, and remarkable antibacterial activities. The sterilization effect of CANF0.04 against Staphylococcus aureus and Escherichia coli exceed 99.9%. Due to low residual LiCl/DMAc and low diffusion of Ag-NPs, the composite film may have potential for applications in food packaging and bacterial barrier.

scholarly journals Copper-Catalyzed Simultaneous Activation of C–H and N–H Bonds: Three-Component One-Pot Cascade Synthesis of Multi­substituted Imidazoles

Synthesis ◽  
2017 ◽  
Vol 50 (02) ◽  
pp. 361-370 ◽  
Author(s):  
Lucio Melone ◽  
Atul Chaskar ◽  
Sachin Pardeshi ◽  
Pratima Sathe ◽  
Kamlesh Vadagaonkar
Keyword(s):  
Copper Sulfate ◽  
Functional Group ◽  
One Pot ◽  
Modular Synthesis ◽  
Simultaneous Activation ◽  
Arylacetic Acids ◽  
The One ◽  
Straightforward Approach

A copper-catalyzed expedient, practical, and straightforward approach for the one-pot three-component modular synthesis of multisubstituted imidazoles has been described by using arylacetic acids, N-arylbenzamidines, and nitroalkanes. The reaction involves simultaneous activation of C–H and N–H bonds of arylacetic acids and N-arylbenzamidines, respectively. The use of inexpensive copper sulfate as a catalyst, readily available starting materials, and Celite-free workup makes this protocol economically viable. Multisubstituted imidazoles were obtained in moderate to good yields with significant functional group tolerance and high regioselectivity.

scholarly journals 1-(4-Nitrophenyl)-1H-1,2,3-Triazole-4-carbaldehyde: Scalable Synthesis and Its Use in the Preparation of 1-Alkyl-4-Formyl-1,2,3-triazoles

Organics ◽  
2021 ◽  
Vol 2 (4) ◽  
pp. 404-414
Author(s):  
Tomas Opsomer ◽  
Kaat Valkeneers ◽  
Ana Ratković ◽  
Wim Dehaen
Keyword(s):  
One Pot ◽  
Complete Hydrolysis ◽  
One Step ◽  
Synthetic Intermediates ◽  
Cornforth Rearrangement ◽  
Scalable Synthesis ◽  
The One ◽  
Novel Applications ◽  
Hydrolysis Of

1,2,3-Triazole-4-carbaldehydes are useful synthetic intermediates which may play an important role in the discovery of novel applications of the 1,2,3-triazole moiety. In this work, a one-step multigram scale synthesis of 4-formyl-1-(4-nitrophenyl)-1H-1,2,3-triazole (FNPT) as a preferred reagent for the synthesis of 1-alkyl-4-formyltriazoles is described, making use of the commercially available 3-dimethylaminoacrolein and 4-nitrophenyl azide. Next, the earlier reported reaction of FNPT with alkylamines is further explored, and for hexylamine, the one-pot sequential cycloaddition and Cornforth rearrangement is demonstrated. In addition, a useful protocol for the in situ diazotization of 4-nitroaniline is provided. This facilitated the complete hydrolysis of rearranged 4-iminomethyl-1,2,3-triazoles and allowed for the recycling of 4-nitrophenyl azide.

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