A solid phase traceless synthesis of 2-arylaminobenzimidazoles

Viktor Krchñák; Jennifer Smith; Josef Vágner

doi:10.1016/S0040-4039(00)02349-2

A solid phase traceless synthesis of 2-arylaminobenzimidazoles

Viktor Krchñák, Jennifer Smith, Josef Vágner

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

39 Scopus citations

Abstract

A solid phase traceless synthesis of 2-arylaminobenzimidazoles in three combinatorial steps is reported that is based on acid lability of N-benzylanilines. MBHA resin was reacted with o-nitrobenzenes, the nitro group was reduced by tin(II) chloride, the resin-bound o-phenylene diamine was treated with isothiocyanates, and the resulting thiourea cyclized by carbodiimide. 2-Arylaminobenzimidazoles were further derivatized with alkyl halides. Target compounds were cleaved from the solid support by TFA or gaseous HF.

Original language	English (US)
Pages (from-to)	1627-1630
Number of pages	4
Journal	Tetrahedron Letters
Volume	42
Issue number	9
DOIs	https://doi.org/10.1016/S0040-4039(00)02349-2
State	Published - Feb 26 2001
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(00)02349-2

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title = "A solid phase traceless synthesis of 2-arylaminobenzimidazoles",

abstract = "A solid phase traceless synthesis of 2-arylaminobenzimidazoles in three combinatorial steps is reported that is based on acid lability of N-benzylanilines. MBHA resin was reacted with o-nitrobenzenes, the nitro group was reduced by tin(II) chloride, the resin-bound o-phenylene diamine was treated with isothiocyanates, and the resulting thiourea cyclized by carbodiimide. 2-Arylaminobenzimidazoles were further derivatized with alkyl halides. Target compounds were cleaved from the solid support by TFA or gaseous HF.",

author = "Viktor Krch{\~n}{\'a}k and Jennifer Smith and Josef V{\'a}gner",

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AU - Krchñák, Viktor

AU - Smith, Jennifer

AU - Vágner, Josef

PY - 2001/2/26

Y1 - 2001/2/26

N2 - A solid phase traceless synthesis of 2-arylaminobenzimidazoles in three combinatorial steps is reported that is based on acid lability of N-benzylanilines. MBHA resin was reacted with o-nitrobenzenes, the nitro group was reduced by tin(II) chloride, the resin-bound o-phenylene diamine was treated with isothiocyanates, and the resulting thiourea cyclized by carbodiimide. 2-Arylaminobenzimidazoles were further derivatized with alkyl halides. Target compounds were cleaved from the solid support by TFA or gaseous HF.

AB - A solid phase traceless synthesis of 2-arylaminobenzimidazoles in three combinatorial steps is reported that is based on acid lability of N-benzylanilines. MBHA resin was reacted with o-nitrobenzenes, the nitro group was reduced by tin(II) chloride, the resin-bound o-phenylene diamine was treated with isothiocyanates, and the resulting thiourea cyclized by carbodiimide. 2-Arylaminobenzimidazoles were further derivatized with alkyl halides. Target compounds were cleaved from the solid support by TFA or gaseous HF.

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EP - 1630

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 9

ER -

A solid phase traceless synthesis of 2-arylaminobenzimidazoles

Abstract

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