We report the preparation of hitherto unprecedented 3-cyanoallyl boronates using condensation of the parent a-boryl aldehyde and nitriles. The resulting allyl boronates have been used to generate a wide range of borylated thiophenes, which represent a valuable class of heterocycles in modern drug discovery. Subsequent Suzuki–Miyaura cross-coupling enabled the synthesis of pharmaceutically impor...

A facile synthesis of 3-methylthio-3-arylamino-2-cyanoacrylates from 3,3-dimethylthioacrylate and aromatic amines or amino pyridines has been achieved in moderate to high yields (64.0% ~ 93.5%) in 30 minutes at 50 degrees C under microwave irradiation. This method is very simple and the reaction conditions are mild, environmentally friendly and more importantly, quick. In the 3-(4,5-dimethylthi...

The synthesis of 4-amino-3-cyano-N-arylpyrazoles A based on a Thorpe-Ziegler cyclization as the key step has been achieved using microwave activation. Via a new diversity-oriented synthetic pathway, these highly functionalized building blocks allowed the access to various heteroaromatic scaffolds such as pyrazolo-pyridines B, pyrazolo-pyrimidines C and pyrazolo-oxadiazoles D. Interestingly, the...

A variety of heteroaromatic compounds, such as substituted pyridines, pyrazoles, indoles, 2-substituted imidazoles, 2-substituted imidazoles, 2-arylbenzazoles and pyrimidin-2(1H)-ones are synthesized by oxidative aromatization using the activated carbon and molecular oxygen system. Mechanistic study focused on the role of activated carbon in the synthesis of 2-arylbenzazoles is also discussed. ...

Isothiazolo[4,3-b]pyridines are known to be endowed with potent affinity for cyclin G associated kinase (GAK). In this paper, we expanded the structure-activity relationship study by broadening the structural variety at position 3 of the isothiazolo[4,3-b]pyridine scaffold. The most potent GAK ligands (displaying Kd values of less than 100 nM) within this series carry an alkoxy group at positio...

The aza-Morita-Baylis-Hillman (azaMBH) reaction has been studied for electronically and sterically deactivated Michael acceptors. It is found that electronically deactivated systems can be converted with electron-rich phosphanes and pyridines as catalysts equally well. For sterically deactivated systems clearly better catalytic turnover can be achieved with pyridine catalysts. This is in accord...

Pyridines carrying heterosubstituents (such as carboxy, amido, amino, alkoxy or trifluoromethyl groups or solely individual halogen atoms) can be readily and site selectively metalated. Subsequent reaction with a suitable electrophile opens rational access to a wealth of new building blocks for the synthesis of biologically active compounds. This approach relies on organometallic methods, which...