Literature DB >> 26232028

Combined isocyanide-based multi-component Ullmann-type reaction: an efficient access to novel nitrogen-containing pentacyclic compounds.

Shima Dianat1, Mohammad Mahdavi2, Setareh Moghimi2, Arash Mouradzadegun1, Abbas Shafiee2, Alireza Foroumadi3.   

Abstract

2-Chloro-3-formyl quinoline has been applied as an aldehyde moiety in the Groebke-Blackburn-Bienaymé multi-component reaction with isocyanides, 2-aminoazines, and 2-aminoazole to afford the desired adducts which are amenable for further cyclization on the basis of Ullmann-type coupling. The copper iodide-mediated intramolecular C-N bond formation in the second step gave an easy access to a series of imidazo[4[Formula: see text],5[Formula: see text]:4,5]pyrrolo[2,3-b]quinoline derivatives in moderate to good yields.

Entities:  

Keywords:  2-Chloro-3-formyl-quinoline; Copper-mediated; Isocyanide-based multi-component reaction (IMCR); Polycyclic heterocycles; Ullmann-type reaction

Mesh：

Substances：

Year:  2015        PMID： 26232028     DOI： 10.1007/s11030-015-9622-2

Source DB:  PubMed          Journal:  Mol Divers        ISSN： 1381-1991            Impact factor:   2.943


  18 in total

1.  Skeletal diverse synthesis of N-fused polycyclic heterocycles via the sequence of Ugi-type MCR and CuI-catalyzed coupling/tandem Pictet-Spengler reaction.

Authors:  Vikas Tyagi; Shahnawaz Khan; Vikas Bajpai; Harsh M Gauniyal; Brijesh Kumar; Prem M S Chauhan
Journal:  J Org Chem       Date:  2012-01-24       Impact factor: 4.354

2.  Efficient entry into hydrazinopeptide-like structures via sequential Ugi reactions.

Authors:  Ekaterina Bushkova; Vladislav Parchinsky; Mikhail Krasavin
Journal:  Mol Divers       Date:  2009-11-10       Impact factor: 2.943

3.  Facile access to functionalized spiro[indoline-3,2'-pyrrole]-2,5'-diones via post-Ugi domino Buchwald-Hartwig/Michael reaction.

Authors:  Nandini Sharma; Zhenghua Li; Upendra K Sharma; Erik V Van der Eycken
Journal:  Org Lett       Date:  2014-07-16       Impact factor: 6.005

4.  Diversity-oriented synthesis of intensively blue emissive 3-hydroxyisoquinolines by sequential Ugi four-component reaction/reductive Heck cyclization.

Authors:  Lisa Moni; Melanie Denissen; Gianluca Valentini; Thomas J J Müller; Renata Riva
Journal:  Chemistry       Date:  2014-11-04       Impact factor: 5.236

5.  IND-2, a pyrimido[1″,2″:1,5]pyrazolo[3,4-b]quinoline derivative, circumvents multi-drug resistance and causes apoptosis in colon cancer cells.

Authors:  Chandrabose Karthikeyan; Crystal Lee; Joshua Moore; Roopali Mittal; Esther A Suswam; Kodye L Abbott; Satyanarayana R Pondugula; Upender Manne; Narayanan K Narayanan; Piyush Trivedi; Amit K Tiwari
Journal:  Bioorg Med Chem       Date:  2014-12-08       Impact factor: 3.641

6.  New synthesis of benzo-delta-carbolines, cryptolepines, and their salts: in vitro cytotoxic, antiplasmodial, and antitrypanosomal activities of delta-carbolines, benzo-delta-carbolines, and cryptolepines.

Authors:  E Arzel; P Rocca; P Grellier; M Labaeïd; F Frappier; F Guéritte; C Gaspard; F Marsais; A Godard; G Quéguiner
Journal:  J Med Chem       Date:  2001-03-15       Impact factor: 7.446

7.  Antitumor polycyclic acridines. 17. Synthesis and pharmaceutical profiles of pentacyclic acridinium salts designed to destabilize telomeric integrity.

Authors:  Jennifer C Cookson; Robert A Heald; Malcolm F G Stevens
Journal:  J Med Chem       Date:  2005-11-17       Impact factor: 7.446

8.  Polycyclic compounds by Ugi-Pictet-Spengler sequence.

Authors:  Wei Wang; Sarah Ollio; Eberhardt Herdtweck; Alexander Dömling
Journal:  J Org Chem       Date:  2010-12-29       Impact factor: 4.354

9.  Novel 7-oxyiminomethyl derivatives of camptothecin with potent in vitro and in vivo antitumor activity.

Authors:  S Dallavalle; A Ferrari; B Biasotti; L Merlini; S Penco; G Gallo; M Marzi; M O Tinti; R Martinelli; C Pisano; P Carminati; N Carenini; G Beretta; P Perego; M De Cesare; G Pratesi; F Zunino
Journal:  J Med Chem       Date:  2001-09-27       Impact factor: 7.446

10.  Synthesis, in vitro cytotoxicity and apoptosis inducing study of 2-aryl-3-nitro-2H-chromene derivatives as potent anti-breast cancer agents.

Authors:  Samira Rahmani-Nezhad; Maliheh Safavi; Mahboobeh Pordeli; Sussan Kabudanian Ardestani; Leila Khosravani; Yaghoub Pourshojaei; Mohammad Mahdavi; Saeed Emami; Alireza Foroumadi; Abbas Shafiee
Journal:  Eur J Med Chem       Date:  2014-09-06       Impact factor: 6.514
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  2 in total

Review 1.  α-Aminoazoles/azines: key reaction partners for multicomponent reactions.

Authors:  Shah Imtiaz; Jahangir Ahmad War; Syqa Banoo; Sarfaraz Khan
Journal:  RSC Adv       Date:  2021-03-16       Impact factor: 3.361

2.  Solvent- and Catalyst-Free One-Pot Green Bound-Type Fused Bis-Heterocycles Synthesis via Groebke-Blackburn-Bienaymé Reaction/SNAr/Ring-Chain Azido-Tautomerization Strategy.

Authors:  Miguel Ángel Claudio-Catalán; Shrikant G Pharande; Andrea Quezada-Soto; Kranthi G Kishore; Angel Rentería-Gómez; Felipe Padilla-Vaca; Rocío Gámez-Montaño
Journal:  ACS Omega       Date:  2018-05-14
  2 in total

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