14301-36-1Relevant articles and documents
13C NMR ANALYSIS OF SOME SIMPLE TETRAHYDROISOQUINOLINES
Mata, Rachel,Chang, Ching-Jer,McLaughlin, Jerry L.
, p. 1263 - 1270 (1983)
13C NMR resonances of 15 simple tetrahydroisoquinolines have been assigned on the basis of chemical shift theory, 13C-1H coupling constants and deuterium labelling at specific positions.The chemical shifts of both aliphatic and aromatic protons were correlated with substituent effects. - Key Words : 13C NMR spectra; cactus alkaloids; simple tetrahydroisoquinolines; carnegine; heliamine; lemaireocereine; longimammatine; lophophorine; N-methylanhalinine; O-methylcorypalline; O-methyluberine; nortehuanine; tehuanine; weberidine.
A concise, regio and stereoselective route to fluorinated protoberberines via tandem addition-cyclisation reactions of phthalide anions with 3,4-dihydroisoquinolines
Warrener, Ronald N.,Liu, Ligong,Russell, Richard A.
, p. 7485 - 7496 (1998)
A series of fluorinated protoberberines have been prepared by condensing fluorinated phthalide anions with 6,7-dimethoxydihydroisoquinoline. The spectroscopy and stereochemistry of the products are discussed and the stereochemical outcome of the reactions rationalised.
One-pot method for preparing 6,7-dimethoxy-3,4-dihydroisoquinoline hydrochloride
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Paragraph 0030; 0043-0054, (2020/03/09)
The invention provides a one-pot method for preparing 6,7-dimethoxy-3,4-dihydroisoquinoline hydrochloride. The method comprises the following steps: with 3,4-dimethoxyphenylethylamine and a formylation reagent as raw materials, carrying out a reaction to prepare an intermediate solution, and subjecting the prepared intermediate solution to a further reaction with a solution containing oxalyl chloride; after the reaction is finished, adding phosphotungstic acid for catalytic cyclization; then adding an alcohol solvent for oxalic acid removal to obtain a target product; and finally, cooling andcrystallizing a reaction solution, carrying out filtering, leaching a filter cake, and carrying out drying to obtain the target product. According to the invention, process operation is extremely simple, and the 6,7-dimethoxy-3,4-dihydroisoquinoline hydrochloride (with a purity of 99.0% or above and a single impurity content of less than or equal to 0.15%) meeting the cGMP quality index requirements and having yield of 75% or above can be obtained only by cooling, filtering, leaching and drying after the one-pot reaction, so process material, manpower and equipment costs are obviously reduced;the process safety level of the method is obviously improved; waste materials are few; and good industrial application prospects are obtained.
Sequential One-Pot Vilsmeier-Haack and Organocatalyzed Mannich Cyclizations to Functionalized Benzoindolizidines and Benzoquinolizidines
Outin, Johanne,Quellier, Pauline,Bélanger, Guillaume
, p. 4712 - 4729 (2020/03/30)
The development of new one-pot sequential cyclizations involving a Vilsmeier-Haack reaction followed by an organocatalyzed Mannich reaction is reported. This synthetic strategy gives access to functionalized indolizidines and quinolizidines in one operation from readily synthesized precursors. Yields and diastereoselectivities are good to excellent when formamides are used to trigger the key step, bearing either an electron-rich aryl or a pyrrole as the nucleophilic partner in the first cyclization.
Mn(II)-Catalyzed N -Acylation of Amines
Ma, Juan,Zhang, Jingyu,Gong, Hang
, p. 693 - 703 (2019/01/23)
A practical protocol has been developed here for the Mn(II)-catalyzed N -acylation of amines with high yields using N, N -dimethylformamide and other amides as the carbonyl source. The protocol is simple, does not require any acid, base, ligand, or other additives, and encompasses a broad substrate scope for primary, secondary, and heterocyclic amines.
