4.7 Article

Modification of Pyrrolo[2,1-a]isoquinolines and Polysubstituted Pyrroles via Methylenation with Acetyl Chloride and Dimethylsulfoxide

Related references

Note: Only part of the references are listed.
Article Chemistry, Organic

Modification of Pyrrolo[2,1-a]isoquinolines and Pyrrolo[1,2-a]quinolines with Ammonium Acetate and Dimethyl Sulfoxide via Methylthiomethylation

Jia-Qin Li et al.

Summary: An efficient methylthiomethylation of pyrroloisoquinolines and pyrroloquinolines has been achieved using ammonium acetate and dimethyl sulfoxide. Moderate to good yields of methylthiomethylated heterocycles can be obtained in most cases, with trace amounts to good yields of methylene-bridged products observed. The chemoselectivity of this process is greatly influenced by the choice of DMSO activator and its amount. It is also noteworthy that the process is scalable and the product can easily be transformed to sulfone and sulfoxide.

JOURNAL OF ORGANIC CHEMISTRY (2022)

Review Chemistry, Organic

Recent progress in the synthesis of pyrrolo[2,1-a]isoquinolines

Hai-Lei Cui

Summary: Pyrrolo[2,1-a]isoquinolines are commonly found in a wide range of bioactive natural products and pharmaceutically important molecules. The synthesis of pyrrolo[2,1-a]isoquinoline derivatives provides an easy and useful approach to create artificial molecules with potential applications. Numerous excellent methodologies for constructing pyrrolo[2,1-a]isoquinolines have been reported in the past decade.

ORGANIC & BIOMOLECULAR CHEMISTRY (2022)

Article Chemistry, Organic

Modification of pyrrolo[2,1-a]isoquinolines via dicarbonylation with dimethyl sulfoxide and arylacyl bromides affording 1,2-dicarbonylated pyrrolo[2,1-a]isoquinolines

Xiao-Hui Chen et al.

Summary: A series of pyrroloisoquinolines have been modified via dicarbonylation with DMSO and arylacyl bromides, yielding highly functionalized 1,2-diketones bearing privileged frameworks in acceptable to good yields (12-73%).

TETRAHEDRON LETTERS (2021)

Article Chemistry, Organic

DMSO as a Dual Carbon Synthon and Water as Oxygen Donor for the Construction of 1,3,5-Oxadiazines from Amidines

Yi Zhang et al.

Summary: This study established a selective and efficient synthesis of diaryl 1,3,5-oxadiazines for the first time from amidines in wet DMSO. The reaction involved the formation of two new C-N and two new C-O bonds, with DMSO acting as a dual carbon synthon and water providing the oxygen atom for constructing the oxadiazine ring.

ORGANIC LETTERS (2021)

Article Chemistry, Organic

Formylation and Bromination of Pyrrolo[2,1-a]isoquinoline Derivatives with Bromoisobutyrate and Dimethyl Sulfoxide

Jia-Qin Li et al.

Summary: An efficient formylation method for pyrroloisoquinolines using bromoisobutyrate and dimethyl sulfoxide as carbonyl reagent has been developed, providing good yields of formylated products (up to 94%) which can be scaled up easily. Additionally, the combination of bromoisobutyrate and dimethyl sulfoxide can also act as a bromination reagent for pyrroloisoquinolines without methoxy groups, yielding brominated products in acceptable to good yields (up to 82%).

JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

DMSO/SOCl2-mediated C(sp2)-H amination: switchable synthesis of 3-unsubstituted indole and 3-methylthioindole derivatives

Jingran Zhang et al.

Summary: The reaction of 2-alkenylanilines with SOCl2 in DMSO selectively affords 3-unsubstituted indoles and 3-methylthioindoles, depending on temperature. At room temperature, 3-unsubstituted indoles are formed through intramolecular cyclization and elimination, while at higher temperature, 3-methylthioindoles are produced via further electrophilic methylthiolation.

CHEMICAL COMMUNICATIONS (2021)

Article Chemistry, Organic

FeCl3 mediated dimerization of dihydropyrrolo[2,1-a]isoquinolines and chlorination of tetrasubstituted pyrroles

Xue-Fei Jiang et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2020)

Article Chemistry, Applied

Direct Synthesis of Dihydropyrrolo[2,1-a]Isoquinolines through FeCl3 Promoted Oxidative Aromatization

Hai-Lei Cui et al.

ADVANCED SYNTHESIS & CATALYSIS (2019)

Review Chemistry, Medicinal

Pyrrolo[2,1-a]isoquinoline scaffold in drug discovery: advances in synthesis and medicinal chemistry

Maria D. Matveeva et al.

FUTURE MEDICINAL CHEMISTRY (2019)

Article Chemistry, Organic

NH4OAc-Promoted Cascade Approach towards Aberrant Synthesis of Chromene-Fused Quinolinones

Santosh Kumari et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2019)

Article Chemistry, Organic

Palladium-Catalyzed Cross-Coupling of Arylboronic Acid and Benzonitriles Using DMSO as the Methylene Source

Han-Jun Ai et al.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2018)

Article Chemistry, Organic

Synthesis of Benzoindolizines through 1,5-Electrocyclization/Oxidation Cascades

Si-Wei Liu et al.

JOURNAL OF ORGANIC CHEMISTRY (2018)

Article Chemistry, Organic

Dimethyl Sulfoxide Involved One-Pot Synthesis of Quinoxaline Derivatives

Caixia Xie et al.

JOURNAL OF ORGANIC CHEMISTRY (2017)

Article Chemistry, Applied

Copper-Catalyzed Coupling of Indoles with Dimethylformamide as a Methylenating Reagent

Fan Pu et al.

ADVANCED SYNTHESIS & CATALYSIS (2016)

Review Chemistry, Applied

The Applications of Dimethyl Sulfoxide as Reagent in Organic Synthesis

Xiao-Feng Wu et al.

ADVANCED SYNTHESIS & CATALYSIS (2016)

Review Chemistry, Organic

Dimethyl Sulfoxide as a Synthon in Organic Chemistry

Ebenezer Jones-Mensah et al.

SYNTHESIS-STUTTGART (2016)

Article Chemistry, Organic

PPh3•HBr-DMSO: A Reagent System for Diverse Chemoselective Transformations

Kanchan Mal et al.

JOURNAL OF ORGANIC CHEMISTRY (2015)

Review Chemistry, Medicinal

Anticancer Properties of Lamellarins

Christian Bailly

MARINE DRUGS (2015)

Article Chemistry, Organic

The ammonium-promoted formylation of indoles by DMSO and H2O

Haiyang Fei et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2013)

Review Chemistry, Organic

SYNTHESIS AND BIOLOGICAL ACTIVITY OF LAMELLARIN ALKALOIDS: AN OVERVIEW

Tsutomu Fukuda et al.

HETEROCYCLES (2011)

Review Chemistry, Multidisciplinary

Beyond the Pummerer Reaction: Recent Developments in Thionium Ion Chemistry

Laura H. S. Smith et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2010)

Review Chemistry, Multidisciplinary

Lamellarins and related pyrrole-derived alkaloids from marine organisms

Hui Fan et al.

CHEMICAL REVIEWS (2008)