Regioselective piperidine-catalyzed tandem imination-isocyanate annulation to fused tricyclic triazines

Indrajeet J. Barve; Chih Hau Chen; Chih Hsien Kao; Chung-Ming Sun

doi:10.1021/co400159z

Regioselective piperidine-catalyzed tandem imination-isocyanate annulation to fused tricyclic triazines

Indrajeet J. Barve, Chih Hau Chen, Chih Hsien Kao, Chung-Ming Sun^*

^*此作品的通信作者

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16 引文斯高帕斯（Scopus）

摘要

A novel tandem imination-isocyanate-mediated annulation was explored. Ionic liquid-immobilized 2-aminobenzimidazoles react sequentially with aldehydes and isocyanates to give highly functionalized benzimidazole-embedded triazines. The second-stage transformation revealed that the formation of triazinone functionality is entirely regioselective to allow rapid assembly of biologically interesting tricyclic skeletons. In conjunction with the application of microwave irradiation and IL support, this method provides an efficient route to access substituted benzoimidazotriazines.

原文	English
頁（從 - 到）	244-249
頁數	6
期刊	ACS Combinatorial Science
卷	16
發行號	5
DOIs	https://doi.org/10.1021/co400159z
出版狀態	Published - 12 5月 2014

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abstract = "A novel tandem imination-isocyanate-mediated annulation was explored. Ionic liquid-immobilized 2-aminobenzimidazoles react sequentially with aldehydes and isocyanates to give highly functionalized benzimidazole-embedded triazines. The second-stage transformation revealed that the formation of triazinone functionality is entirely regioselective to allow rapid assembly of biologically interesting tricyclic skeletons. In conjunction with the application of microwave irradiation and IL support, this method provides an efficient route to access substituted benzoimidazotriazines.",

keywords = "benzoimidazotriazine, imination, ionic liquid, isocyanate-mediated annulation, microwave, tandem reaction",

author = "Barve, {Indrajeet J.} and Chen, {Chih Hau} and Kao, {Chih Hsien} and Chung-Ming Sun",

year = "2014",

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doi = "10.1021/co400159z",

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T1 - Regioselective piperidine-catalyzed tandem imination-isocyanate annulation to fused tricyclic triazines

AU - Barve, Indrajeet J.

AU - Chen, Chih Hau

AU - Kao, Chih Hsien

AU - Sun, Chung-Ming

PY - 2014/5/12

Y1 - 2014/5/12

N2 - A novel tandem imination-isocyanate-mediated annulation was explored. Ionic liquid-immobilized 2-aminobenzimidazoles react sequentially with aldehydes and isocyanates to give highly functionalized benzimidazole-embedded triazines. The second-stage transformation revealed that the formation of triazinone functionality is entirely regioselective to allow rapid assembly of biologically interesting tricyclic skeletons. In conjunction with the application of microwave irradiation and IL support, this method provides an efficient route to access substituted benzoimidazotriazines.

AB - A novel tandem imination-isocyanate-mediated annulation was explored. Ionic liquid-immobilized 2-aminobenzimidazoles react sequentially with aldehydes and isocyanates to give highly functionalized benzimidazole-embedded triazines. The second-stage transformation revealed that the formation of triazinone functionality is entirely regioselective to allow rapid assembly of biologically interesting tricyclic skeletons. In conjunction with the application of microwave irradiation and IL support, this method provides an efficient route to access substituted benzoimidazotriazines.

KW - benzoimidazotriazine

KW - imination

KW - ionic liquid

KW - isocyanate-mediated annulation

KW - microwave

KW - tandem reaction

UR - http://www.scopus.com/inward/record.url?scp=84900431920&partnerID=8YFLogxK

U2 - 10.1021/co400159z

DO - 10.1021/co400159z

M3 - Article

C2 - 24646395

AN - SCOPUS:84900431920

SN - 2156-8952

VL - 16

SP - 244

EP - 249

JO - ACS Combinatorial Science

JF - ACS Combinatorial Science

IS - 5

ER -

Regioselective piperidine-catalyzed tandem imination-isocyanate annulation to fused tricyclic triazines

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