Literature DB >> 21731115

Microwave-assisted multicomponent reaction in water leading to highly regioselective formation of benzo[f]azulen-1-ones.

Shu-Liang Wang1, Chuang Cheng, Fei-Yue Wu, Bo Jiang, Feng Shi, Shu-Jiang Tu, Trideep Rajale, Guigen Li.   

Abstract

Microwave-assisted three-component reaction has been established for the regioselective synthesis of benzo[f]azulen-1-ones. The reaction was performed in aqueous media under microwave irradiation by using readily available and inexpensive starting materials. A total of 38 examples were examined to show a broad substrate scope and good overall yields (70-89%). The present new synthesis shows attractive green chemistry characteristics, such as the use of water as reaction media, concise one-pot conditions, short reaction periods (7-24 min), easy work-up/purification and reduced waste production without the use of any strong acids or metal promoters.

Entities:  

Year:  2011        PMID: 21731115      PMCID: PMC3124679          DOI: 10.1016/j.tet.2011.05.002

Source DB:  PubMed          Journal:  Tetrahedron        ISSN: 0040-4020            Impact factor:   2.457


  38 in total

1.  Microwave-enhanced aminocarbonylations in water.

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Journal:  Org Lett       Date:  2005-07-21       Impact factor: 6.005

Review 2.  Microwave-assisted synthesis in water as solvent.

Authors:  Doris Dallinger; C Oliver Kappe
Journal:  Chem Rev       Date:  2007-04-24       Impact factor: 60.622

3.  A new domino autocatalytic reaction leading to polyfunctionalized spiro[5.5]undecanes and dispiro[4.2.5.2]pentadecanes.

Authors:  Bo Jiang; Wen-Juan Hao; Jin-Peng Zhang; Shu-Jiang Tu; Feng Shi
Journal:  Org Biomol Chem       Date:  2009-04-03       Impact factor: 3.876

4.  Four-component domino reaction leading to multifunctionalized quinazolines.

Authors:  Bo Jiang; Shu-Jiang Tu; Parminder Kaur; Walter Wever; Guigen Li
Journal:  J Am Chem Soc       Date:  2009-08-26       Impact factor: 15.419

5.  Unsaturated gamma-lactones. Relationship between their structure and antimicrobial activity.

Authors:  A Dal Pozzo; A Dansi; E Meneghini
Journal:  Boll Chim Farm       Date:  1974-05

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Authors:  K Rehse; U Emisch
Journal:  Arch Pharm (Weinheim)       Date:  1983       Impact factor: 3.751

7.  [Protein binding of drugs determined by continuous ultrafiltration III: Protein binding of anticoagulant tetronic acids (author's transl)].

Authors:  K Rehse; M Rothe; M Kühn
Journal:  Arch Pharm (Weinheim)       Date:  1982-01       Impact factor: 3.751

8.  Organocatalytic asymmetric synthesis of polyfunctionalized 3-(cyclohexenylmethyl)-indoles via a quadruple domino Friedel-Crafts-type/Michael/Michael/aldol condensation reaction.

Authors:  Dieter Enders; Chuan Wang; Meruyert Mukanova; Andreas Greb
Journal:  Chem Commun (Camb)       Date:  2010-03-08       Impact factor: 6.222

9.  Highly diastereoselective domino synthesis of 6-spirosubstituted pyrido[2,3-d]pyrimidine derivatives in water.

Authors:  Bo Jiang; Long-Ji Cao; Shu-Jiang Tu; Wen-Rui Zheng; Hai-Zhu Yu
Journal:  J Comb Chem       Date:  2009 Jul-Aug

10.  Novel multicomponent one-pot synthesis of tetrahydro-1H-1,5-benzodiazepine-2-carboxamide derivatives.

Authors:  Ahmad Shaabani; Ali Maleki; Hamid Mofakham
Journal:  J Comb Chem       Date:  2008-06-14
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  5 in total

Review 1.  Advancements in tetronic acid chemistry. Part 2: Use as a simple precursor to privileged heterocyclic motifs.

Authors:  Moaz M Abdou; Rasha A El-Saeed; Khaled M Elattar; Zeynel Seferoğlu; John Boukouvalas
Journal:  Mol Divers       Date:  2016-06-27       Impact factor: 2.943

2.  Microwave-Assisted Expeditious Synthesis of 2-Alkyl-2-(N-arylsulfonylindol-3-yl)-3-N-acyl-5-aryl-1,3,4-oxadiazolines Catalyzed by HgCl₂ under Solvent-Free Conditions as Potential Anti-HIV-1 Agents.

Authors:  Zhiping Che; Yuee Tian; Shengming Liu; Jia Jiang; Mei Hu; Genqiang Chen
Journal:  Molecules       Date:  2018-11-10       Impact factor: 4.411

Review 3.  Microwave-assisted multicomponent reactions in heterocyclic chemistry and mechanistic aspects.

Authors:  Shivani Gulati; Stephy Elza John; Nagula Shankaraiah
Journal:  Beilstein J Org Chem       Date:  2021-04-19       Impact factor: 2.883

Review 4.  Recent application of visible-light induced radicals in C-S bond formation.

Authors:  Vishal Srivastava; Pravin K Singh; Arjita Srivastava; Praveen P Singh
Journal:  RSC Adv       Date:  2020-05-27       Impact factor: 4.036

Review 5.  Microwave-Assisted Syntheses of Bioactive Seven-Membered, Macro-Sized Heterocycles and Their Fused Derivatives.

Authors:  Mohsine Driowya; Aziza Saber; Hamid Marzag; Luc Demange; Khalid Bougrin; Rachid Benhida
Journal:  Molecules       Date:  2016-08-09       Impact factor: 4.411

  5 in total

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