Literature DB >> 34054151

Ultrasound assisted one-pot synthesis of benzo-fused indole-4, 9-dinones from 1,4-naphthoquinone and α-aminoacetals.

Quang H Luu1, Jorge D Guerra1, Cecilio M Castañeda1, Manuel A Martinez1, Jong Saunders1, Benjamin A Garcia2, Brenda V Gonzales2, Anushritha R Aidunuthula2, Shizue Mito1,2.   

Abstract

A one-pot synthesis of benzo[f]indole-4,9-diones from 1,4-naphthoquinone with α-aminoacetals has been developed. This method provides a straightforward synthesis of benzo[f]indole-4,9-diones via intramolecular nucleophilic attack of aminoquinones to aldehydes under mild reaction conditions. The detailed mechanism was also investigated.

Entities:  

Keywords:  Cyclization; Heterocycles; One-pot reaction; Ultrasound-assisted; p-Indolequinone

Year:  2016        PMID： 34054151      PMCID： PMC8158052          DOI： 10.1016/j.tetlet.2016.04.031

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  14 in total

1.  INDQ/NO, a bioreductively activated nitric oxide prodrug.

Authors:  Kavita Sharma; Aishwarya Iyer; Kundan Sengupta; Harinath Chakrapani
Journal:  Org Lett       Date:  2013-05-09       Impact factor: 6.005

2.  Synthesis of murrayaquinone-A.

Authors:  K Matsuo; S Ishida
Journal:  Chem Pharm Bull (Tokyo)       Date:  1994-06       Impact factor: 1.645

3.  One-pot synthesis of benzo[f]indole-4,9-diones from 1,4-naphthoquinones and terminal acetylenes.

Authors:  Mitsuaki Yamashita; Kazunori Ueda; Koichi Sakaguchi; Harukuni Tokuda; Akira Iida
Journal:  Chem Pharm Bull (Tokyo)       Date:  2011       Impact factor: 1.645

4.  Biological evaluation of donor-acceptor aminonaphthoquinones as antitumor agents.

Authors:  Julio Benites; Jaime A Valderrama; Karina Bettega; Rozangela Curi Pedrosa; Pedro Buc Calderon; Julien Verrax
Journal:  Eur J Med Chem       Date:  2010-10-14       Impact factor: 6.514

5.  Novel syntheses of murrayaquinone A and furostifoline through 4-oxygenated carbazoles by allene-mediated electrocyclic reactions starting from 2-chloroindole-3-carbaldehyde.

Authors:  H Hagiwara; T Choshi; J Nobuhiro; H Fujimoto; S Hibino
Journal:  Chem Pharm Bull (Tokyo)       Date:  2001-07       Impact factor: 1.645

6.  A Biomimetic Approach to the Discorhabdin Alkaloids: Total Syntheses of Discorhabdins C and E and Dethiadiscorhabdin D.

Authors:  Kelly Marshall Aubart; Clayton H. Heathcock
Journal:  J Org Chem       Date:  1999-01-08       Impact factor: 4.354

7.  Synthesis of indolequinones from bromoquinones and enamines mediated by Cu(OAc)2.H2O.

Authors:  Martyn Inman; Christopher J Moody
Journal:  J Org Chem       Date:  2010-09-03       Impact factor: 4.354

8.  Synthesis and antitumor evaluation of analogues of the marine pyrroloiminoquinone tsitsikammamines.

Authors:  Arnaud Rives; Benjamin Le Calvé; Tamara Delaine; Laurent Legentil; Robert Kiss; Evelyne Delfourne
Journal:  Eur J Med Chem       Date:  2009-10-14       Impact factor: 6.514

9.  Concise synthesis of heterocycle-fused naphthoquinones by employing sonogashira coupling and tandem addition-elimination/intramolecular cyclization.

Authors:  Kazunori Ueda; Mitsuaki Yamashita; Koichi Sakaguchi; Harukuni Tokuda; Akira Iida
Journal:  Chem Pharm Bull (Tokyo)       Date:  2013       Impact factor: 1.645

10.  Bexarotene prodrugs: targeting through cleavage by NQO1 (DT-diaphorase).

Authors:  Anja Schäfer; Ethan S Burstein; Roger Olsson
Journal:  Bioorg Med Chem Lett       Date:  2014-03-13       Impact factor: 2.823
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