Efficient synthesis of 1,3,5-oxygenated synthons from dimethyl 3-oxoglutarate: first use of borane-dimethyl sulfide complex as a regioselective reducing agent of 3-oxygenated glutarate derivatives

Abstract

A redução seletiva do 3-oxoglutarato de dimetila foi realizada em vários níveis. A redução quimiosseletiva da carbonila cetônica com boridreto de sódio é descrita em alto rendimento, fornecendo o 3-hidroxiglutarato de dimetila. Quando o complexo borana-dimetil sulfeto (BMS) foi empregado como agente redutor, um diol ou um triol puderam ser obtidos, respectivamente, a partir do 3-hidróxi-ou do 3-oxoglutarato, permitindo a síntese de compostos 1,3,5-oxigenados prática e eficientemente.The selective reduction of dimethyl 3-oxoglutarate was accomplished in different levels. A high yielding sodium borohydride reduction of the keto group is fully described leading to dimethyl 3-hydroxyglutarate. When borane-dimethyl sulfide (BMS) complex was used, a diol or a triol compound can be obtained by selective or total reduction of 3-hydroxy-or 3-oxoglutarate, respectively, allowing an efficient and practical route to 1,3,5-oxygenated compounds.

Synthetic Access to Benzimidacarbocyanine Dyes to Tailor Their Aggregation Properties

“…The crude product (3.0742 g, 76% yield) was used without further purification. Spectral characterizations matched those found in the literature. , …”

“…This experiment was adapted from literature protocols. , Dimethyl-1,3-acetonedicarboxylate (4.0135 g, 23.046 mmol) was placed in a 50 mL RBF along with methanol (∼20 mL). The resulting clear and colorless solution was cooled in an ice bath prior to the portionwise addition of sodium borohydride (0.2517 g, 6.645 mmol).…”

“…Spectral characterizations matched those found in the literature. 49,50 1,3-Bis(2-benzimidazolyl)propan-2-ol (12). o-Phenylenediamine (3.7325 g, 34.515 mmol) was combined with 3-hydroxypentanedioic acid dimethyl ester (3.0395 g, 17.253 mmol) in a 50 mL RBF.…”