199477-91-3

Upstream product

• 2459-07-6 methyl pyridine-2-carboxylate 
• 64-04-0 phenethylamine 
• 98-98-6 2-Picolinic acid 
• 2524-52-9 ethyl-2-picolinate 
• 39901-94-5 2-picolinoyl chloride hydrochloride 
• 1121-60-4 pyridine-2-carbaldehyde 
• 1622923-53-8 potassium 2-isonicotinoyltrifluoroborate 

Downstream Products

• 496-15-1 1-indoline 
• 1373618-68-8 C₁₆H₁₈N₂O₃ 
• 120-72-9 indole 
• 1381861-25-1 C₁₄H₁₁IN₂O 
• 1381861-26-2 C₁₆H₁₅IN₂O₃ 
• 1403672-82-1 C₂₁H₁₇ClN₂O₂ 
• 98-98-6 2-Picolinic acid 
• 1610539-79-1 (E)-methyl 2-(7-oxo-6-phenethyl-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-ylidene)acetate 
• 65846-46-0 5-phenyl-2-(pyridin-2-yl)oxazole 
• 1196-38-9 3,4-dihydroisoquinolin-1(2H)-one 

Relevant academic research and scientific papers

Cobalt-Catalyzed C(sp2)-H Carbonylation of Amino Acids Using Picolinamide as a Traceless Directing Group

Herein we report an efficient protocol for the C(sp2)-H carbonylation of amino acid derivatives based on an inexpensive cobalt(II) salt catalyst. Carbonylation was accomplished using picolinamide as a traceless directing group, CO (1 atm) as the carbonyl

Visible Light-Driven Efficient Synthesis of Amides from Alcohols using Cu?N?TiO2 Heterogeneous Photocatalyst

Amides were synthesized from alcohols and amines in high yields using an in situ generated active ester of N-hydroxyimide with our developed Cu?N?TiO2 catalyst at room temperature using oxygen as a sole oxidant under visible light. The catalyst can be easily prepared, robust, and recycled four times without a considerable change in catalytic activity. This developed protocol applies to a wide substrate scope and has good functional group tolerance. The application of this amidation reaction has been successfully demonstrated for the synthesis of moclobemide, an antidepressant drug, and an analog of the itopride drug on a gram scale.

Rhodium-Catalyzed Copper-Assisted Intermolecular Domino C?H Annulation of 1,3-Diynes with Picolinamides: Access to Pentacyclic π-Extended Systems

A new mode of reactivity of 1,3-diynes in rhodium-catalyzed oxidative annulation reactions has enabled the rapid assembly of extended π systems from readily available picolinamide derivatives. The process involves a double C?H bond activation and the iterative annulation of two 1,3-diyne units, with each alkyne moiety engaged in an orchestrated insertion sequence with high regiocontrol, leading to the formation of five new C?C bonds and the construction of four fused rings in a single operation. Either isoquinoline-1-carboxamides or fused polycyclic systems can be accessed by a switch in the regioselectivity of the second diyne insertion depending on the reaction conditions. DFT theoretical calculations have elucidated that the cooperative participation of both rhodium and copper in substrate activation, favored in the presence of excess of the copper(II) salt, is key to such a reversal of regioselectivity and subsequent multiple cyclization leading to fused polycyclic products. The role of copper was found to be essential in assisting both multiple insertion and rhodium-walking sequences, with the implication of intermediates with a Rh?Cu bond (2.60 ?).

[Cp*RhIII] in an Ionic Liquid as a Highly Efficient and Recyclable Catalytic Medium for Regio- and Diastereoselective Csp3–H Carbenoid Insertion

Reported herein is a bidentate-assisted Csp3–H bond insertion using Cp*RhIII/IL as a highly efficient and recyclable catalytic medium, while showing good functional group tolerance. Notably, the application of ionic liquid not only lowered the temperature, but also enhanced the diastereoselectivity of this reaction. This work significantly expanded the scope of ionic liquids in Csp3–H functionalizations.

Direct Amidation of Carboxylic Acids through an Active α-Acyl Enol Ester Intermediate

The development of a highly efficient and simple protocol for the direct amidation of carboxylic acids is described employing ynoates as novel coupling reagents. The transformation proceeds in good to excellent yields via in situ α-acyl enol ester intermediates formation under mild reaction conditions. This useful method has been demonstrated for a range of substrates to provide a succinct access to structurally diverse amides, including key intermediates of glibenclamide, tiapride hydrochloride, and nateglinide, and can be conducted on a mole scale.

Chemoselective acylation of primary amines and amides with potassium acyltrifluoroborates under acidic conditions

Current methods for constructing amide bonds join amines and carboxylic acids by dehydrative couplings-processes that usually require organic solvents, expensive and often dangerous coupling reagents, and masking other functional groups. Here we describe an amide formation using primary amines and potassium acyltrifluoroborates promoted by simple chlorinating agents that proceeds rapidly in water. The reaction is fast at acidic pH and tolerates alcohols, carboxylic acids, and even secondary amines in the substrates. It is applicable to the functionalization of primary amides, sulfonamides, and other N-functional groups that typically resist classical acylations and can be applied to late-stage functionalizations.

Synthesis of alkylidene pyrrolo[3,4-b]pyridin-7-one derivatives via Rh III-catalyzed cascade oxidative alkenylation/annulation of picolinamides

A practical RhIII-catalyzed cascade olefination/annulation of picolinamides leading to pyrrolo[3,4-b]pyridines has been developed. The reaction shows wide scope, complete regiocontrol and excellent stereoselectivity. This journal is the Partner Organisations 2014.

Lanthanum(III) triflate catalyzed direct amidation of esters

Lanthanum trifluoromethanesulfonate is an effective single-component catalyst for synthesizing a variety of amides directly from esters and amines under mild conditions. Highly selective amidation of esters and amines, as well as catalyst-controlled amidation of esters, demonstrated the effectiveness of the catalyst system.

Iodination of remote ortho-C-H bonds of arenes via directed S EAr: A streamlined synthesis of tetrahydroquinolines

A new strategy for the synthesis of tetrahydroquinolines (THQs) via the sequential functionalizations of remote C-H bonds is reported. This method uses a single picolinamide directing/protecting group to effect Pd-catalyzed γ-C(sp3)-H arylation, metal-free ε-C(sp2)-H iodination, and Cu-catalyzed intramolecular C-N cross-coupling. The overall sequence is efficient and versatile, and offers a streamlined synthesis of THQs with complex substitution patterns from readily available aryl iodide and aliphatic amine precursors.

Zinc(II)-catalyzed oxidative amidation of arylaldehydes with alkylamines under solvent-free conditions

The first zinc-catalyzed oxidative amidation of arylaldehydes has been developed. Various amides were prepared in good yields under solvent-free and mild reaction conditions.