ChemInform Abstract: 5‐(Diazomethyl)tetrazoles Substituted in Position 1 or 2 ‐ A Comparative Study.

Abstract

168ChemInform Abstract The hitherto unknown title compounds (I) and (II) -readily obtained by Bamford-Stevens reaction (preferred method) -show expected differences in both spectroscopic (UV/VIS, IR) and reactive behavior. The reactions a) with acids such as (V), electrophiles such as isatin (XI), or cycloaddition partners such as (XII) or (XIII) (generated in situ) lead to the products (VII)-(X), (IIIa)-(IIIc), (IVa)-(IVc) whereas b) the reactive behavior towards nucleophiles such as cyanide (XIV) or carbene formation under thermolytic conditions leads to the production of the compounds (IIId), (IIIe), (IIIf), (IVd). -Due to the more electron-withdrawal of the tetrazolyl system of (I), the isomers (I) react more slowly than (II) in the cases a) while the order is reverse in the cases b). (Products (IVe), (IVf) analogous to (IIIe), (IIIf) are not isolated from the reaction of (IIc) with (XV) or (XVI).) -The compounds (I) exhibit a certain sensitivity towards aqueous alkali (loss of the CHN2 function).

Matrix Metalloproteinase Inhibitors Containing a [(Carboxyalkyl)amino]zinc Ligand: Modification of the P1 and P2' Residues

“…5-Methoxy-2-(dimethoxymethyl)benzaldehyde (32). A solution of the dimethyl acetal of p-anisaldehyde 30 (5.3 g, 29.1 mmol) in dry diethyl ether (90 mL) at 0 °C was treated with tert-butyllithium (20.5 mL, 1.7 M in hexanes, 34.9 mmol).…”