As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO248,mainly used in chemical industry, its synthesis route is as follows.,37441-50-2
Step2 A strong glass tube was charged with Pd2(dba)3 (6.4 mg; 0.007 mmol), xantphos (12 mg; 0.02 mmol), 1,2-thiazinane-1,1-dioxide (115 mg; 0.85 mmol), and Cs2CO3 (323 mg; 0.99 mmol).The tube was capped with a rubber septum, evacuated and backfilled with nitrogen. 6-Bromo-1-methyl-1H-indole carboxylic acid ethyl ester (200 mg; 0.71 mmol) in 1 ml of 1,4-dioxane was added through the septum.The septum was replaced with a Teflon screwcap.The tube was sealed, and the mixture was stirred at 100 C. for 64 hours.The reaction mixture was cooled to room temperature, diluted with ethyl acetate (10 ml), filtered, and concentrated in vacuo.The crude material was purified by flash chromatography (silica gel, ethyl acetate-hexane 1:1) to afford 190 mg (66%; m/z 337) of colorless crystals.This compound was dissolved in a mixture of tetrahydrofuran (4 ml), methanol (2 ml) and water (1 ml).To this solution was added dropwise LiOH monohydrate (95 mg; 2.26 mmol) dissolved in 1 ml water and the mixture was stirred at room temperature for 16 h.The reaction mixture was partition between ethyl acetate and water.The aqueous layer was acidified with 2N HCl to ph ~3-4 and extracted with ethyl acetate.The organic layer was washed with brine and dried (Na2SO4) and evaporated in vacuo.Yield 131 mg of 6-(1,1-Dioxo-1lambda6-[1,2]thiazinan-2-yl)-1-methyl-1H-indole-2-carboxylic acid as a white powder (75%); m/z 307.
With the complex challenges of chemical substances, we look forward to future research findings about 1,2-Thiazinane 1,1-dioxide,belong thiazines compound
Reference£º
Patent; Bamberg, Joe Timothy; Gabriel, Tobias; Krauss, Nancy Elisabeth; Mirzadegan, Taraneh; Palmer, Wylie Solang; Smith, David Bernard; US2004/77646; (2004); A1;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem