22774-32-9

Upstream product

• 106-49-0 p-toluidine 
• 106-96-7 propargyl bromide 
• 16156-58-4 prop-2-yn-1-ol methanesulfonate 
• 116507-14-3 N-(5-methoxy-2-furfuryl)-p-toluidine 

Relevant academic research and scientific papers

Pyrrolylmethyl functionalized o-carborane derivatives

The reactions of the 16e half-sandwich complex CpCoS2C2B10H10 (1), diazo esters, and various 1,6-diynes (3a-i; PhN(CH2C CH)2, 4-Me-PhN(CH2C CH)2, 4-OMe-PhN(CH2C CH)2, 4-F-PhN(CH2C CH)2, BzN(CH2C CH)2, O(CH2C CH)2, C(Ac)2(CH2C CH)2, N(CH2C CH)3, NH(CH2C CH)N(CH2C CH)2) were investigated, in which two novel types of B-H activated products CpCoS2B10H9(CH2CO2Et)C5H3N(R)(CHCHCO2Et) (4a-c; R = Ph, 4-Me-Ph, 4-OMe-Ph) and the key intermediate CpCoS2B10H9(CHCO2Me) (CH2CO2Me) (9) were isolated. 9 features a reactive Co-B bond, which triggers insertion of various 1,6-diynes to further lead to different final products. Substrates 3a-c are activated by the Co-B bond to produce o-carborane derivatives 4a-c which are functionalized by a cobalt-complexed 3-pyrrolylmethyl group. The pyrrole ring is formed by in situ ring closure of 1,6-diynes. Control experiments and isolation of the intermediate CpCoS2B10H9(CHCO2Me)(CH2CO2Me)HCC CH2N(4-Me-Ph)(CH2C CH) (10) support the proposed mechanism concerning the formation of 4a-c analogues by oxidation. All of the new complexes were characterized by NMR, IR, elemental analysis, and mass spectrometry. The structures of 4a-6a and 9 were determined by single-crystal X-ray diffraction analysis as well.

The deptq+ experiment: Leveling the dept signal intensities and clean spectral editing for determining chn multiplicities

We propose a new13C DEPTQ+ NMR experiment, based on the improved DEPTQ experiment, which is designed to unequivocally identify all carbon multiplicities (Cq, CH, CH2, and CH3) in two experiments. Compared to this improved DEPTQ exper

Synthesis and characterization of N,N-di(prop-2-ynyl)-p-toluidine

In order to investigate the intramolecular [4 + 2] cycloaddition, we prepared some new tertiary N-(5-substituted-2-furfuryl)-N-prop-2-ynyl-p- toluidines [Hergold-Brundic et al., Acta Cryst C56:e520, 2000; Mance and Jakopcic, Mol Divers 9:229, 2005; Mance,

Preparation and cyclization of some N-(2,2-Dimethylpropargyl) homo- And heteroaromatic amines and the synthesis of some pyrido[2,3-d]pyrimidines

The Cu(I) catalyzed cyclization of o-substituted N-(2,2-dimethylpropargyl) anilines yields 8-substituted 2,2-dimethyl-1,2-dihydroquinolines, while m-substituted analogues provide a mixture of 5- and 7-substituted dihydroquinoline systems. This reaction can be extended to 2-amino-N-(2,2- dimethylpropargyl)anthracene, yielding a dihydronaphtho[2,3-f]quinoline product, and to aminoquinoline derivatives, which yield substituted phenanthroline products. Pyridine analogues did not cyclize, apparently because of complexation with the copper reagent. An alternative synthetic approach to these cyclized products, when complexation may be a problem, is illustrated by the following example. 2-Chloro-4-N-(2,2-dimethylpropargyl)pyrimidine was reduced using a Lindlar catalyst to the corresponding alkene which did not undergo an amino-Claisen rearrangement. However, the 5-bromopyrimidine alkene analogue underwent addition with phenylselanyl bromide to give a product that cyclized, using butyllithium, to a pyrido[2,3-d]pyrimidine selenium-containing product from which the selenium moiety could be removed to yield either a dihydro- or a tetrahydro-pyrido[2,3-d]pyrimidine system. A Heck reaction on the 5-bromopyrimidine alkene gave a 5-methylene-6,7-dihydro-5H-pyrrolo[2,3-d] pyrimidine. CSIRO 2005.

Direct and selective N-monoalkynylation and N-monoalkenylation of anilines with alky(e)nyl methanesulfonates using methylmagnesium bromide as a base

Several anilines were directly N-monoalkynylated and N-monoalkenylated with alkynyl methanesulfonates and alkenyl methanesulfonates, respectively, using methylmagnesium bromide as a base in good yields with high selectivities.

SELECTIVE SYNTHESIS OF MONO- AND DIPROPARGYLARYLAMINES ON ALUMINUM OXIDE

Propargylarylamines are formed with preparative yields in the reaction of propargyl bromide with arylamines in a molar ratio of 1:3 on aluminum oxide.The use of aluminum oxide modified with potassium carbonate and a reduction in the relative amount of the