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Synthesis of isoquinolines and heterocycle-fused …

N2 - Reaction of 1-(3-cyanopropoxy)-3,4-dihydronaphthalene-2-carbonitriles with potassium tert-butoxide gave 5-amino-1,2,6,7-tetrahydrobenzo[f]furo[2,3-c] isoquinolines via a Truce-Smiles rearrangement. The 5-amino group was transformed to the bromo derivatives which were allowed to react with aliphatic cyclic amines to produce amino derivatives. In contrast, a combination of imidazole and NaH gave a dihydrofuran ring cleaved product, the structure of which was confirmed by X-ray crystallographic analysis. Effects of the newly synthesized compounds on carbamylcholine chloride-induced contractions of trachea and lipoprotein lipase mRNA expression were also evaluated and found one promising bronchodilator.

Reaction of 1-(3-cyanopropoxy)-3,4-dihydronaphthalene-2-carbonitriles with potassium tert-butoxide gave 5-amino-1,2,6,7-tetrahydrobenzo[f]furo[2,3-c] isoquinolines via a Truce-Smiles rearrangement. The 5-amino group was transformed to the bromo derivatives which were allowed to react with aliphatic cyclic amines to produce amino derivatives. In contrast, a combination of imidazole and NaH gave a dihydrofuran ring cleaved product, the structure of which was confirmed by X-ray crystallographic analysis. Effects of the newly synthesized compounds on carbamylcholine chloride-induced contractions of trachea and lipoprotein lipase mRNA expression were also evaluated and found one promising bronchodilator.

Synthesis of Isoquinolines by the Pomeranz-Fritsch Reaction

SYNTHESIS OF 1,4-DISUBSTITUTED ISOQUINOLINES AS …

A facile synthesis of the C4-substituted isoquinolines 5a-c and 6a-c is described. Commercially available 4-bromoisoquinoline is converted to the -unsaturated esters 8 and 10 on treatment with the appropriate acrylate ester under Heck reaction conditions. The saturated amides 5a-c were obtained from the reaction of ester 9 with the requisite primary amine. Similarly the unsaturated analogues 6a-c were prepared by reacting ester 10 with the appropriate amine. The cytotoxicity of the target molecules was evaluated in two tumour cell lines . Two compounds, 6b and 6c, showed sufficient activity in the human non-small cell lung cancer line NSCLC-N16-L16 to be worthy of further study.

In conclusion, we managed to synthesize (±)-5,6-dihydro-6-phenylindolo[2,1-a]isoquinolin-5-ol and ethyl indolo[2,1-a]isoquinoline-6-carboxylate using theSuzuki-Miyaura cross coupling reaction and specific reaction conditions, usingthe base KOtBu, for the formation of aromatic rings, both as key steps.

A Novel Method for the Synthesis of Indolo[2,1-a]isoquinolines

In this dissertation we discuss the synthesis of(±)-5,6-dihydro-6-phenylindolo[2,1-a]isoquinolin-5-ol and ethyl indolo[2,1-a]isoquinoline-6-carboxylate using these reaction conditions as our key steps.

The utilization of sequential palladium-catalyzed α-arylation andcyclization reactions provides a general approach to an array ofisoquinolines and their corresponding N-oxides.

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ChemSynthesis - Chemical Database


Indole synthesis - Organic chemistry

In our laboratories, a variety of indolo[2,1-a]isoquinolines, for example 5,12-dimethyl-6-phenylindolo[2,1-a]isoquinoline, have been synthesized using theSuzuki-Miyaura cross coupling reaction and reaction conditions for theformation of aromatic rings (KOBut in DMF and a light source – developed inour laboratories) as key steps.

Benzyne Click Chemistry: Synthesis of Benzotriazoles …

AB - Reaction of 1-(3-cyanopropoxy)-3,4-dihydronaphthalene-2-carbonitriles with potassium tert-butoxide gave 5-amino-1,2,6,7-tetrahydrobenzo[f]furo[2,3-c] isoquinolines via a Truce-Smiles rearrangement. The 5-amino group was transformed to the bromo derivatives which were allowed to react with aliphatic cyclic amines to produce amino derivatives. In contrast, a combination of imidazole and NaH gave a dihydrofuran ring cleaved product, the structure of which was confirmed by X-ray crystallographic analysis. Effects of the newly synthesized compounds on carbamylcholine chloride-induced contractions of trachea and lipoprotein lipase mRNA expression were also evaluated and found one promising bronchodilator.

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