Literature DB >> 24249920

Syntheses of Benzo[b]furan-6-carbonitrile and 6-Cyanobenzo[b]furan-2-boronic Acid Pinacol Ester.

John D Williams1, Xiaoyuan Ding, Son Nguyen, Kimberly K Vines, Norton P Peet.   

Abstract

6-Cyanobenzo[b]furan-2-boronic acid pinacol ester (10) is a potentially useful 2-point scaffold for the construction of specific compounds or compound libraries with benzofuran cores. Using a per-iodination/de-iodination strategy coupled with a Sonogashira alkynylation and Cu-catalyzed heteroannulation, we have developed a procedure that allows the preparation of benzo[b]furan-6-carbonitrile (9) and 6-cyanobenzo[b]furan-2-boronic acid pinacol ester (10) in gram quantities.

Entities:  

Keywords:  Benzo[b]furan; Sonogashira alkynylation; heteroannulation; heterocycle synthesis

Year:  2013        PMID： 24249920      PMCID： PMC3829476          DOI： 10.1080/00397911.2012.684086

Source DB:  PubMed          Journal:  Synth Commun        ISSN： 0039-7911            Impact factor:   2.007


  6 in total

1.  New 2-substituted 1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine having highly active and potent central alpha 2-antagonistic activity as potential antidepressants.

Authors:  L E Kennis; F P Bischoff; C J Mertens; C J Love; F A Van den Keybus; S Pieters; M Braeken; A A Megens; J E Leysen
Journal:  Bioorg Med Chem Lett       Date:  2000-01-03       Impact factor: 2.823

2.  One-pot synthesis of arylboronic acids and aryl trifluoroborates by Ir-catalyzed borylation of arenes.

Authors:  Jaclyn M Murphy; C Christoph Tzschucke; John F Hartwig
Journal:  Org Lett       Date:  2007-02-03       Impact factor: 6.005

3.  Nonreductive deiodination of ortho-iodo-hydroxylated arenes using tertiary amines.

Authors:  Rahul Subhash Talekar; Grace Shiahuy Chen; Shin-Yu Lai; Ji-Wang Chern
Journal:  J Org Chem       Date:  2005-10-14       Impact factor: 4.354

4.  Potent and selective non-benzodioxole-containing endothelin-A receptor antagonists.

Authors:  A S Tasker; B K Sorensen; H S Jae; M Winn; T W von Geldern; D B Dixon; W J Chiou; B D Dayton; S Calzadila; L Hernandez; K C Marsh; J R WuWong; T J Opgenorth
Journal:  J Med Chem       Date:  1997-01-31       Impact factor: 7.446

5.  Discovery of N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]furo[2,3-c]pyridine-5-carboxamide, an agonist of the alpha7 nicotinic acetylcholine receptor, for the potential treatment of cognitive deficits in schizophrenia: synthesis and structure--activity relationship.

Authors:  Donn G Wishka; Daniel P Walker; Karen M Yates; Steven C Reitz; Shaojuan Jia; Jason K Myers; Kirk L Olson; E Jon Jacobsen; Mark L Wolfe; Vincent E Groppi; Alexander J Hanchar; Bruce A Thornburgh; Luz A Cortes-Burgos; Erik H F Wong; Brian A Staton; Thomas J Raub; Nicole R Higdon; Theron M Wall; Raymond S Hurst; Rodney R Walters; William E Hoffmann; Mihaly Hajos; Stanley Franklin; Galen Carey; Lisa H Gold; Karen K Cook; Steven B Sands; Sabrina X Zhao; John R Soglia; Amit S Kalgutkar; Stephen P Arneric; Bruce N Rogers
Journal:  J Med Chem       Date:  2006-07-13       Impact factor: 7.446

6.  Rational design, synthesis, and structure-activity relationships of novel factor Xa inhibitors: (2-substituted-4-amidinophenyl)pyruvic and -propionic acids.

Authors:  Kazuyuki Sagi; Tadakiyo Nakagawa; Masahiro Yamanashi; Shingo Makino; Mitsuo Takahashi; Masaru Takayanagi; Kaoru Takenaka; Nobuyasu Suzuki; Seiji Oono; Noriyasu Kataoka; Kohki Ishikawa; Sayaka Shima; Yumiko Fukuda; Takashi Kayahara; Shunji Takehana; Yoichiro Shima; Kazumi Tashiro; Hiroshi Yamamoto; Ryota Yoshimoto; Seinosuke Iwata; Takashi Tsuji; Kuniya Sakurai; Masataka Shoji
Journal:  J Med Chem       Date:  2003-05-08       Impact factor: 7.446
  6 in total

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