• Bulletin of the Korean Chemical Society
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• 제23권11호
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• pp.1623-1628
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• 2002

Tetracyclic pyrido[2,3-b]azepine derivatives 4a-d and 4f as analogues of mirtazapine were synthesized via N-acyliminium ion cyclization by using aromatic rings such as benzene and thiophene ring as a ${\pi}-nucleophile$, and evaluated for the binding affinity for ${\alpha}2-adrenoceptor$. Among tested compounds, 2,3,9,13b-tetrahydro-1H-benzo[f]pyrrolo[2,1-a]pyrido[2,3-c]azepine (4a) was the most potent (Ki = 0.26 ${\mu}M)$ but showed about 3-fold less binding affinity than mirtazapine (Ki = 0.08 ${\mu}M)$ for a2-adrenoceptor.

• 대한약학회:학술대회논문집
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• 대한약학회 2002년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.2
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• pp.350.2-350.2
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• 2002

The reaction of N-acyliminium ion with a variety of nucleophiles is one of the powerful method to introduce various substituents at the a-carbon of an amine. Particularly this type of inter and intramolecular C-C bond formation can be effectively applied to the synthesis of the bioactive natural or unnatural compounds as well as many bioactive peptidomimetics. Accordingly. much attention has been devoted to the practical and efficient methods for the generation of acyliminium ion precursors though there are many important aspects in the reaction involving N-acyliminium ions. (omitted)

• Bulletin of the Korean Chemical Society
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• 제32권10호
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• pp.3738-3742
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• 2011

Bismuth tribromide ($BiBr_3$) catalyzed Mannich-type reactions of N-acyliminium ions which generated in situ from N-benzyloxycarbonylamino p-tolylsulfones have been developed. In the presence of catalytic amount of $BiBr_3$, N-benzyloxycarbonylamino p-tolylsulfones prepared from aromatic and aliphatic aldehydes reacted with silyl enol ether and silyl enol ester under mild reaction conditions to afford N-Cbz-protected ${\beta}$-amino ketones and N-Cbz-protected ${\beta}$-amino esters in moderate to good yield, respectively.

• Bulletin of the Korean Chemical Society
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• 제15권4호
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• pp.278-279
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• 1994

• Bulletin of the Korean Chemical Society
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• 제29권4호
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• pp.755-757
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• 2008

A short and highly efficient synthetic method to prepare synthetically useful tetrahydroindolizinone derivatives from the ring-closing metathesis of N-allyl-5-allyl-5-hydroxylactams is described.

• Bulletin of the Korean Chemical Society
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• 제25권12호
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• pp.1924-1928
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• 2004

Allylations of N-benzyl and N-methyl cyclic imides were accomplished successfully under mild Barbier type conditions using zinc metal, allyl bromide and catalytic amount of $PbBr_2$. Subsequent coupling reactions with some carbon nucleophiles afforded 1,2- and 1,4-addition products in moderate to high yields.

• Bulletin of the Korean Chemical Society
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• 제28권8호
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• pp.1401-1404
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• 2007

An efficient Pictet-Spengler type reaction of N,O-acetal TMS ethers for the practical synthesis of 1-substituted tetrahydroquinolines, medicinally important alkaloids, has been accomplished. To demonstrate the versatility of this novel procedure, the total synthesis of calycotomine, a representative 1-hydroxymethyl substituted tetrahydroisoquinoline, is also described.