Literature DB >> 22971137

One-pot synthesis of pyrrolo[1,2-a]quinoxaline derivatives via iron-promoted aryl nitro reduction and aerobic oxidation of alcohols.

Maria de Fatima Pereira1, Valérie Thiéry.   

Abstract

Here, we describe a new one-pot method to synthesize 4,7-substituted pyrrolo[1,2-a]quinoxalines and related heterocyles through a cascade of redox reactions/imine formation/intramolecular cyclization. This procedure tolerates readily available substituted 1-(2-nitrophenyl)pyrrole derivatives and aliphatic or benzylic alcohols as starting materials using iron powder and acidic conditions. This is the first example of constructing N-heterocycles via iron-mediated aryl nitro reduction and aerobic oxidation of alcohols in one pot.

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Year:  2012        PMID: 22971137     DOI: 10.1021/ol302006b

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  4 in total

1.  α-Hydroxy acid as an aldehyde surrogate: metal-free synthesis of pyrrolo[1,2-a]quinoxalines, quinazolinones, and other N-heterocycles via decarboxylative oxidative annulation reaction.

Authors:  Mayavan Viji; Manjunatha Vishwanath; Jaeuk Sim; Yunjeong Park; Chanhyun Jung; Seohu Lee; Heesoon Lee; Kiho Lee; Jae-Kyung Jung
Journal:  RSC Adv       Date:  2020-10-07       Impact factor: 4.036

2.  Novel total syntheses of oxoaporphine alkaloids enabled by mild Cu-catalyzed tandem oxidation/aromatization of 1-Bn-DHIQs.

Authors:  Bo Zheng; Hui-Ya Qu; Tian-Zhuo Meng; Xia Lu; Jie Zheng; Yun-Gang He; Qi-Qi Fan; Xiao-Xin Shi
Journal:  RSC Adv       Date:  2018-08-14       Impact factor: 4.036

3.  Iron-catalyzed one-pot synthesis of quinoxalines: transfer hydrogenative condensation of 2-nitroanilines with vicinal diols.

Authors:  Ramachandra Reddy Putta; Simin Chun; Seok Beom Lee; Junhwa Hong; Dong-Chan Oh; Suckchang Hong
Journal:  RSC Adv       Date:  2021-05-20       Impact factor: 3.361

4.  Tin(ii) chloride dihydrate/choline chloride deep eutectic solvent: redox properties in the fast synthesis of N-arylacetamides and indolo(pyrrolo)[1,2-a]quinoxalines.

Authors:  Sergio Alfonso Trujillo; Diana Peña-Solórzano; Oscar Rodríguez Bejarano; Cristian Ochoa-Puentes
Journal:  RSC Adv       Date:  2020-11-06       Impact factor: 3.361

  4 in total

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