Elemental sulfur mediated synthesis of pyrrolo[1,2-α]quinoxalines from 1-(2-nitroaryl) pyrroles

Synthesis ◽  
2021 ◽  
Author(s):  
Tung Nguyen ◽  
Tuan Ho ◽  
Nam T. S. Phan ◽  
Nhu Phan ◽  
Thuyen Ho ◽  
...  
Keyword(s):  
Transition Metals ◽  
Elemental Sulfur ◽  
Coupling Reagents ◽  
Benzyl Alcohols ◽  
Fused Heterocycles ◽  
Arylacetic Acids ◽  
Harsh Conditions

Methods to afford pyrrolo[1,2-α]quinoxalines often require the use of prefunctionalized aniline precursors, transition metals, and/or harsh conditions. Herein we describe a simple coupling of 1-(2-nitroaryl)pyrroles and arylacetic acids, in the presence of elemental sulfur, to furnish the fused heterocycles in good yields. The conditions were compatible with many functionalities including ester, nitrile, halogen, and nitro groups. Use of benzyl alcohols and picoline coupling reagents was also attempted.

scholarly journals Functionalization of C–H bonds in acetophenone oximes with arylacetic acids and elemental sulfur

RSC Advances ◽  
2020 ◽  
Vol 10 (19) ◽  
pp. 11024-11032 ◽  
Author(s):  
Phuc H. Pham ◽  
Khang X. Nguyen ◽  
Hoai T. B. Pham ◽  
Thien T. Tran ◽  
Tung T. Nguyen ◽  
...  
Keyword(s):  
Transition Metals ◽  
Elemental Sulfur ◽  
Arylacetic Acids ◽  
Acetophenone Oxime

Annulation of acetophenone oxime acetates, arylacetic acids or esters, and elemental sulfur in absence of transition metals is reported.

Sulfur-Mediated Decarboxylative Coupling of 2-Nitrobenzyl Alcohols and Arylacetic Acids

Synlett ◽  
2020 ◽  
Vol 31 (11) ◽  
pp. 1112-1116
Author(s):  
Tung T. Nguyen ◽  
Nam T. S. Phan ◽  
Khang X. Nguyen ◽  
Duyen K. Nguyen ◽  
Phuc H. Pham ◽  
...  
Keyword(s):  
Transition Metals ◽  
Nitrogen Source ◽  
Elemental Sulfur ◽  
New Method ◽  
Complex Structures ◽  
Reaction Conditions ◽  
Mild Conditions ◽  
Decarboxylative Coupling ◽  
Arylacetic Acids

We report a new method for the synthesis of substituted quinazolines by the condensation of 2-nitrobenzyl alcohols with arylacetic acids. The transformation requires the use of urea as a nitrogen source, elemental sulfur as a promoter, DABCO as a base, and DMSO as a solvent. Functionalities such as chloro, fluoro, trifluoromethyl, thienyl, and indolyl groups were all compatible with the reaction conditions. Because our method uses stable simple substrates to obtain the N,N-heterocycles in the absence of transition metals, it offers a potential pathway for preparing complex structures under mild conditions.

Elemental Sulfur Mediated Decarboxylative Redox Cyclization Reaction of o-Chloronitroarenes and Arylacetic Acids

2015 ◽  
Vol 17 (4) ◽  
pp. 976-978 ◽  
Author(s):  
Tirumaleswararao Guntreddi ◽  
Rajeshwer Vanjari ◽  
Krishna Nand Singh
Keyword(s):  
Elemental Sulfur ◽  
Cyclization Reaction ◽  
Arylacetic Acids

ChemInform Abstract: Elemental Sulfur Mediated Decarboxylative Redox Cyclization Reaction of o-Chloronitroarenes and Arylacetic Acids.

ChemInform ◽  
2015 ◽  
Vol 46 (28) ◽  
pp. no-no
Author(s):  
Tirumaleswararao Guntreddi ◽  
Rajeshwer Vanjari ◽  
Krishna Nand Singh
Keyword(s):  
Elemental Sulfur ◽  
Cyclization Reaction ◽  
Arylacetic Acids

scholarly journals Hydroxylamine-mediated C–C amination via an aza-hock rearrangement

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Tao Wang ◽  
Philipp M. Stein ◽  
Hongwei Shi ◽  
Chao Hu ◽  
Matthias Rudolph ◽  
...  
Keyword(s):  
Transition Metals ◽  
Benzyl Alcohol ◽  
Substituted Anilines ◽  
Reaction Conditions ◽  
Benzyl Alcohols ◽  
Simple Route ◽  
Reduction Sequence

AbstractDespite the widespread use of anilines, synthetic challenges to these targets still exist. Selectivity is often an issue, when using the traditional nitration-reduction sequence or more modern approaches, including arene C–H aminations catalyzed by transition metals, photosensitizers, or electrodes. Accordingly, there is still a need for general methods to rapidly, directly access specific isomers of substituted anilines. Here, we report a simple route towards the synthesis of such motifs starting from benzyl alcohols, which are converted to anilines by the use of arylsulfonyl hydroxylamines, via an aza-Hock rearrangement. Good to excellent yields are observed. The method is applicable to various benzyl alcohol surrogates (such as ethers, esters, and halides) as well as simple alkylarenes. Functionalizations of pharmaceutically relevant structures are feasible under the reaction conditions. Over ten amination reagents can be used, which facilitates the rapid assembly of a vast set of compounds.

Synthesis of 2-Arylbenzothiazol-5-amines from N,N-Dialkyl-3-nitroanilines

Synlett ◽  
2020 ◽  
Vol 31 (18) ◽  
pp. 1813-1816 ◽  
Author(s):  
Tung T. Nguyen ◽  
Nam T. S. Phan ◽  
Hang T. Pham ◽  
Tuan H. Ho ◽  
Duy Q. Do ◽  
...  
Keyword(s):  
Elemental Sulfur ◽  
Reaction Conditions ◽  
Simple Method ◽  
Simple Route ◽  
Arylacetic Acids ◽  
Derivatives Of

AbstractWe report a simple method for coupling of N,N-dialkyl-3-nitroarenes, elemental sulfur, and activated sp3 C–H bonds in 2-methylazaarenes or arylacetic acids to afford derivatives of 2-arylbenzothiazol-5-amines. Only DABCO base was required, and many heterocycles such as imidazoles, oxazoles, quinolines, and thiophenes were compatible with the reaction conditions. Our approach offers a simple route to useful substituted thiazol-5-amines from commercially available nitroarenes.

Elemental Sulfur-Mediated Decarboxylative Redox Cyclization ­Reaction: Copper-Catalyzed Synthesis of 2-Substituted Benzo­thiazoles

Synlett ◽  
2017 ◽  
Vol 29 (02) ◽  
pp. 219-224 ◽  
Author(s):  
Xin Wang ◽  
Xiaotong Li ◽  
Renhe Hu ◽  
Zhao Yang ◽  
Ren Gu ◽  
...  
Keyword(s):  
Functional Groups ◽  
Elemental Sulfur ◽  
Antitumor Drug ◽  
Cyclization Reaction ◽  
Copper Metal ◽  
Wide Range ◽  
Ligand Free ◽  
Arylacetic Acids ◽  
Scale Experiment

A S8-mediated directed decarboxylative redox-cyclization strategy for the synthesis of 2-substituted benzothiazoles from o-iodoanilines, arylacetic acids, and elemental sulfur catalyzed by cheap copper metal has been developed. This reaction is operationally simple, ligand-free, compatible with a wide range of functional groups, and provides the desired products in good to excellent yields. In addition, a gram-scale experiment was carried out to furnish PMX 610, an antitumor drug.

Indium-catalyzed direct preparation of dibenzyl sulfides from benzyl alcohols and elemental sulfur with a hydrosilane and its application to the preparation of dibenzyl selenide

2016 ◽  
Vol 57 (6) ◽  
pp. 676-679 ◽  
Author(s):  
Takahiro Miyazaki ◽  
Masahiro Katayama ◽  
Shunsuke Yoshimoto ◽  
Yohei Ogiwara ◽  
Norio Sakai
Keyword(s):  
Elemental Sulfur ◽  
Benzyl Alcohols ◽  
Direct Preparation

NH4I-promoted oxidative formation of benzothiazoles and thiazoles from arylacetic acids and phenylalanines with elemental sulfur

2021 ◽  
Author(s):  
Yujia Xia ◽  
Huawen Huang ◽  
Wei Hu ◽  
Guo-Jun Deng
Keyword(s):  
Catalytic System ◽  
Elemental Sulfur ◽  
Three Component Reaction ◽  
Arylacetic Acids

A NH4I/K3PO4-based catalytic system has been established to enable oxidative formation of thiazole compounds from arylacetic acids and phenylalanines with elemental sulfur. While the three-component reaction of anilines or β-naphthylamines...

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