2020
DOI: 10.1055/s-0040-1707236
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Large-Scale Synthesis of 2-Chlorotetrahydroquinoline and 2-Chlorotetrahydroquinolin-8-one

Abstract: An efficient large-scale preparation of 2-chlorotetrahydroquinoline with cyclohexanone and benzylamine as starting materials was developed and well optimized, in which benzyl-protected enamide was successfully cyclized and benzyl group was directly removed under Vilsmeier conditions. Azeotropic distillation provided 264 g of 2-chlorotetrahydroquinoline (79%) on a 2 mol scale of reaction without intermediate isolation. The downstream product 2-chlorotetrahydroquinolin-8-one was acquired through Boekelheide rear… Show more

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Cited by 7 publications
(3 citation statements)
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“…Over the years, our group has been focusing on developing novel ligands for 3d metal catalysis. 27 Based on the previous bidentate or tridentate geometry-constrained iminopyridyl cobalt complexes as the catalysts for the efficient and highly selective hydrosilylations of monoalkynes 27 a and 1,3-diynes 27 e with primary and secondary silanes, we have reckoned that the cobalt complexes could be extended in the catalytic hydrosilylative reduction of amides. Herein, we report that our developed tridentate geometry-constrained NNN -Co complexes have been successfully employed as efficient catalysts for the hydrosilylative reduction of secondary amides to their corresponding amines with low-cost polymethylhydrosiloxane (PMHS) as the reductant.…”
Section: Introductionmentioning
confidence: 99%
“…Over the years, our group has been focusing on developing novel ligands for 3d metal catalysis. 27 Based on the previous bidentate or tridentate geometry-constrained iminopyridyl cobalt complexes as the catalysts for the efficient and highly selective hydrosilylations of monoalkynes 27 a and 1,3-diynes 27 e with primary and secondary silanes, we have reckoned that the cobalt complexes could be extended in the catalytic hydrosilylative reduction of amides. Herein, we report that our developed tridentate geometry-constrained NNN -Co complexes have been successfully employed as efficient catalysts for the hydrosilylative reduction of secondary amides to their corresponding amines with low-cost polymethylhydrosiloxane (PMHS) as the reductant.…”
Section: Introductionmentioning
confidence: 99%
“…In Liu's work, a copper-catalyzed multicomponent reaction involving sulfonyl azides, alkynes, and allylamines 127 was conducted to obtain 2,3-dihydro-1 H -imidazo-[1,2- a ]indoles 128 in moderate yields. 88 In this reaction, the triazole intermediate is obtained and then decomposes into the ketenimine with the loss of nitrogen. This step is similar to the mechanism described in section 2.3.…”
Section: Multicomponent Reactions Of Azides To Construct Other N-hete...mentioning
confidence: 99%
“…A Cu( i )-catalyzed three-component reaction of alkynes, sulfonyl azides and allylamines offering 2,3-dihydro-1 H -imidazo-[1,2- a ]indoles was reported ( Scheme 43 ). 49 2,3-Dihydro-1 H -imidazo[1,2- a ]indoles were obtained in moderate yields via sequential copper-catalyzed azide–alkyne cycloaddition (CuAAC) followed by a double copper-catalyzed C–N coupling reactions in one-pot.…”
Section: Synthesis Of Heterocyclesmentioning
confidence: 99%