10.1021/je60061a002
The study focuses on the preparation of high-purity model compounds resulting from the reduction of 2,4,6-trinitrotoluene (TNT) for comparison with biodegradation products. The researchers aimed to produce 12 reduction products of TNT, including amino, hydroxylamino, azo, and azoxy compounds. They successfully synthesized eight compounds, two of which, 4,4',6,6'-tetranitro-2,2'-azoxytoluene and 2,4'-dimethyl-3,3',5,5'-tetranitro-ONN-azoxybenzene, are newly reported. The study details the preparation methods and improvements made in the purity of these compounds. Key chemicals involved include 2,4,6-trinitrotoluene (TNT) as the starting material, and various reagents such as m-chloroperoxybenzoic acid, ammonium sulfide, and sodium hypochlorite used in the reduction and oxidation processes to produce the desired compounds. The study also discusses the challenges and modifications made to existing methods to achieve high-purity products.
10.1016/j.tetlet.2014.07.043
The study presents an optimized biomimetic method for the conversion of various α-amino acids to aldehydes using sodium hypochlorite (NaOCl), which serves as an oxidizing agent for the decarboxylation of amino acids. The aldehyde products can then be transformed into tetrahydroisoquinolines, either racemic or (S)-enantiomer forms, through the Pictet–Spengler reaction with dopamine. The study utilizes a phosphate buffer to maximize regioselectivity for the racemic products and a maleic acid buffer for the enantioselective enzymatic synthesis of (S)-enantiomer products using norcoclaurine synthase. The purpose of these chemicals is to facilitate the synthesis of tetrahydroisoquinolines, which are found in numerous natural products and synthetic compounds with pharmacological activity, including benzoisoquinoline alkaloids. The study aims to synthesize novel BIAs with potential pharmacological utility by employing precursor-directed biosynthesis, avoiding the need for chromatography and ensuring the preparations are free of toxic chemical species.
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