Advances in the directed metallation of azines and diazines (pyridines, pyrimidines, pyrazines, pyridazines, quinolines, benzodiazines and carbolines). Part 1: Metallation of pyridines, quinolines and carbolines

Practical and efficient synthesis of orthogonally protected constrained 4-guanidinoprolines.

Ghrelin, a gut-derived orexigenic hormone, is an endogenous ligand of the growth hormone secretagogue receptor (GHS-R). Centrally administered ghrelin has been shown to cause hunger and increase food intake in rodents. Inhibition of ghrelin actions with ghrelin antibody, peptidyl GHS-R antagonists, and antisense oligonucleosides resulted in weight loss and food intake decrease in rodents. Here we report the effects of GHS-R antagonists, some of which were potent, selective, and orally bioavailable. A structure-activity relationship study led to the discovery of 8a, which was effective in decreasing food intake and body weight in several acute rat studies.

2,4-Diaminopyrimidine Derivatives as Potent Growth Hormone Secretagogue Receptor Antagonists

It is shown that t-BuLi in Et(2)O promotes an exclusive regioselective metalation of 2-aryl-6-chloropyridine compounds at the aromatic ortho position demonstrating that the 2-chloropyridyl moiety may be considered as a directing group. This functionally directed metalation group was successfully used for the selective lithiation of substituted aromatics and for the straightforward preparation of new N,P ligands.

First regioselective ortho-lithiation induced by a 2-chloropyridyl group complexation.

Practical routes toward the synthesis of 2-halo- and 2-alkylamino-4-pyridinecarboxaldehydes

Synthesis of Protected 5-Formylpyrido[2,3-d]pyrimidine via a 2,3,4-Trisubstituted Pyridine Using an ortho-Lithiation Strategy; Application to the Synthesis of a Folate Derivative

Novel Pyrrolo[2,3-d]pyrimidine Ring forming Methodology

A short, succinct route to biologically active and medicinally important pyrrolo[2,3-d]pyrimidines has been developed starting from readily available acyclic aldehydes. A very efficienttwo step sequence involving a Knoevenagel condensation followed by copper mediated 1,4-conjugate of vinyl magnesium bromide sets up the acyclic precursor. Then, guanidine cyclization followed by a palliduim catalyzed amination reaction or ozonolytic cleavage of the vinyl substituent followed by guanidine cyclization and intramolecular imine formation complete the synthesis.

Novel Pyrrolo[2,3‐d]pyrimidine Ring Forming Methodology.

Synthesis of Protected 5-Formylpyrido[2,3-d]pyrimidine via a 2,3,4-Trisubstituted Pyridine Using an ortho-Lithiation Strategy; Application to the Synthesis of a Folate Derivative.

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Synthesis of Protected 5-Formylpyrido[2,3-d]pyrimidine via a 2,3,4-Trisubstituted Pyridine Using an ortho-Lithiation Strategy; Application to the Synthesis of a Folate Derivative

Novel Pyrrolo[2,3-d]pyrimidine Ring forming Methodology

Novel Pyrrolo[2,3‐d]pyrimidine Ring Forming Methodology.

Synthesis of Protected 5-Formylpyrido[2,3-d]pyrimidine via a 2,3,4-Trisubstituted Pyridine Using an ortho-Lithiation Strategy; Application to the Synthesis of a Folate Derivative.