A solid-phase traceless synthesis of tetrahydroquinoxalines

Viktor Krchňák; Jennifer Smith; Josef Vágner

doi:10.1016/S0040-4039(01)00197-6

A solid-phase traceless synthesis of tetrahydroquinoxalines

Viktor Krchňák, Jennifer Smith, Josef Vágner

Research output: Contribution to journal › Article › peer-review

30 Scopus citations

Abstract

A solid-phase traceless synthesis of tetrahydroquinoxalines with three combinatorial steps is reported. An aldehyde functionalized polystyrene resin was reductively aminated by amino alcohols, and then the resin bound secondary amines were reacted with o-fluoronitrobenzenes. The hydroxy group was mesylated and the nitro group was reduced by tin(II) chloride to the anilines, which spontaneously cyclized. The secondary aniline nitrogen of the resulting tetrahydroquinoxalines was further derivatized with acyl chlorides and isocyanates. After acidolytic cleavage from the resin, tetrahydroquinoxalines with three points of diversity were obtained.

Original language	English (US)
Pages (from-to)	2443-2446
Number of pages	4
Journal	Tetrahedron Letters
Volume	42
Issue number	13
DOIs	https://doi.org/10.1016/S0040-4039(01)00197-6
State	Published - Mar 26 2001
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "A solid-phase traceless synthesis of tetrahydroquinoxalines",

abstract = "A solid-phase traceless synthesis of tetrahydroquinoxalines with three combinatorial steps is reported. An aldehyde functionalized polystyrene resin was reductively aminated by amino alcohols, and then the resin bound secondary amines were reacted with o-fluoronitrobenzenes. The hydroxy group was mesylated and the nitro group was reduced by tin(II) chloride to the anilines, which spontaneously cyclized. The secondary aniline nitrogen of the resulting tetrahydroquinoxalines was further derivatized with acyl chlorides and isocyanates. After acidolytic cleavage from the resin, tetrahydroquinoxalines with three points of diversity were obtained.",

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year = "2001",

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doi = "10.1016/S0040-4039(01)00197-6",

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T1 - A solid-phase traceless synthesis of tetrahydroquinoxalines

AU - Krchňák, Viktor

AU - Smith, Jennifer

AU - Vágner, Josef

PY - 2001/3/26

Y1 - 2001/3/26

N2 - A solid-phase traceless synthesis of tetrahydroquinoxalines with three combinatorial steps is reported. An aldehyde functionalized polystyrene resin was reductively aminated by amino alcohols, and then the resin bound secondary amines were reacted with o-fluoronitrobenzenes. The hydroxy group was mesylated and the nitro group was reduced by tin(II) chloride to the anilines, which spontaneously cyclized. The secondary aniline nitrogen of the resulting tetrahydroquinoxalines was further derivatized with acyl chlorides and isocyanates. After acidolytic cleavage from the resin, tetrahydroquinoxalines with three points of diversity were obtained.

AB - A solid-phase traceless synthesis of tetrahydroquinoxalines with three combinatorial steps is reported. An aldehyde functionalized polystyrene resin was reductively aminated by amino alcohols, and then the resin bound secondary amines were reacted with o-fluoronitrobenzenes. The hydroxy group was mesylated and the nitro group was reduced by tin(II) chloride to the anilines, which spontaneously cyclized. The secondary aniline nitrogen of the resulting tetrahydroquinoxalines was further derivatized with acyl chlorides and isocyanates. After acidolytic cleavage from the resin, tetrahydroquinoxalines with three points of diversity were obtained.

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U2 - 10.1016/S0040-4039(01)00197-6

DO - 10.1016/S0040-4039(01)00197-6

M3 - Article

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SN - 0040-4039

VL - 42

SP - 2443

EP - 2446

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 13

ER -

A solid-phase traceless synthesis of tetrahydroquinoxalines

Abstract

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