Palladium-Catalysed Intramolecular C–N versus C–C Coupling: The Effect of 1,8-peri-Interaction in the Naphthalene System

Palladium-Catalysed Intramolecular C–N versus C–C Coupling: The Effect of 1,8-peri-Interaction in the Naphthalene System

Abstract Palladium-catalysed competitive intramolecular C–N and C–C coupling of 2-amino-2′-bromodiarylsulfones has been carried out based on 1,8-peri-interactions for the synthesis of phenothiazinedioxide and benzonaphthathiophenedioxide derivatives. A DFT study has been performed that provides supp...

Full description

Bibliographic Details
Main Authors:	Sudarshan Debnath, Shovan Mondal
Format:	Article
Language:	English
Published:	Georg Thieme Verlag KG 2019-01-01
Series:	SynOpen
Subjects:	naphthalene 1,8-peri-interaction cyclization fused-ring heterocycles
Online Access:	http://www.thieme-connect.de/DOI/DOI?10.1055/s-0037-1611667

Similar Items

Synthesis of ([1,2,4]triazolo[4,3-a]pyridin-3-ylmethyl)phosphonates and their benzo derivatives via 5-exo-dig cyclization
by: Aleksandr S. Krylov, et al.
Published: (2019-07-01)

Synthesis of New Pyrazolothiazole Derivatives from 4-Thiazolidinones
by: Nuket Ocal, et al.
Published: (2007-09-01)

Crystal structure of 2,7-diethoxy-1,8-bis(4-nitrobenzoyl)naphthalene
by: Saki Mohri, et al.
Published: (2014-09-01)

Intramolecular C(sp3)–H Bond Amination Strategies for the Synthesis of Saturated N-containing Heterocycles
by: Jiayu Zhang, et al.
Published: (2020-11-01)

A Structurally Diverse Heterocyclic Library by Decoration of Oxcarbazepine Scaffold
by: Giovanni Palmisano, et al.
Published: (2013-11-01)

Synthesis of ethoxy dibenzooxaphosphorin oxides through palladium-catalyzed C(sp2)–H activation/C–O formation
by: Seohyun Shin, et al.
Published: (2014-05-01)

Reagent-controlled regiodivergent intermolecular cyclization of 2-aminobenzothiazoles with β-ketoesters and β-ketoamides
by: Irwan Iskandar Roslan, et al.
Published: (2017-12-01)

Aldol elaboration of 4,5,6,7-tetrahydroisoxazolo[4,3-c]pyridin-4-ones, masked precursors to acylpyridones
by: Raymond C. F. Jones, et al.
Published: (2012-02-01)

Synthesis of a Spirocyclic Oxetane-Fused Benzimidazole
by: Michael Gurry, et al.
Published: (2015-07-01)

Transition-Metal-Free [3+2] Dehydration Cycloaddition of Donor-Acceptor Cyclopropanes With 2-Naphthols
by: Hua Zhao, et al.
Published: (2021-07-01)

Synthesis of Medium-Sized Heterocycles by Transition-Metal-Catalyzed Intramolecular Cyclization
by: Mickael Choury, et al.
Published: (2020-07-01)

A Convenient Approach to Heterocyclic Building Blocks: Synthesis of Novel Ring Systems Containing a [5,6]Pyrano[2,3-c]pyrazol-4(1H)-one Moiety
by: Wolfgang Holzer, et al.
Published: (2007-01-01)

New Route to 3-Alkylthiazolo[3,2-a]benzimidazole Derivatives
by: Nicolas Vanthuyne, et al.
Published: (2005-02-01)

Schiff Bases and Triazolothiadiazines Derived from A Thiophene-Substituted 4-Amino-3-Mercapto-1,2,4-Triazole
by: Roman Gheorghe
Published: (2019-12-01)

Palladium-Catalyzed intramolecular sp3 C–H functionalization : studies in cyclopropyl and heterocyclic motifs
by: Ladd, Carolyn L.
Published: (2018)

Synthesis of Oxazinanones: Intramolecular Cyclization of Amino Acid-Derived Diazoketones via Silica-Supported HClO4 Catalysis
by: Rafael D. C. Gallo, et al.
Published: (2019-02-01)

Synthesis of Substituted α-Trifluoromethyl Piperidinic Derivatives
by: Sarah Rioton, et al.
Published: (2017-03-01)

Dipyrazolo[1,5-a:4',3'-c]pyridines – a new heterocyclic system accessed via multicomponent reaction
by: Wolfgang Holzer, et al.
Published: (2012-12-01)

Naphthalene substituted benzo[c]coumarins: Synthesis, characterization and evaluation of antibacterial activity and cytotoxicity
by: Patel Mrugesh, et al.
Published: (2019-12-01)

2-(4-Pentyloxyphenyl)benzothiazole
by: Yasodha Sivasothy, et al.
Published: (2009-08-01)

Synthesis of 2-(4-Propyloxyphenyl)benzothiazole
by: Yasodha Sivasothy, et al.
Published: (2009-07-01)

The chemistry of 1H-cyclobuta[de]naphthalenes /
by: Friedli, Floyd Ely
Published: (1978)

Intramolecular Nicholas Reaction Enables the Stereoselective Synthesis of Strained Cyclooctynes
by: Diego M. Monzón, et al.
Published: (2021-03-01)

Synthesis of Fused-Ring Compounds through Gold-Catalyzed Cascade Reactions
by: Naoe, Saori
Published: (2016)

Synthesis of Indoles via Intermolecular and Intramolecular Cyclization by Using Palladium-Based Catalysts
by: Ayesha, et al.
Published: (2021-08-01)

Part I, Aromatic annelation : synthesis of naphthalenes ; Part II, C-glycosyl anthraquinone synthesis : total synthesis of vineomycinone B2 methyl ester
by: Gomez Galeno, Jorge E
Published: (2009)

The synthesis of derivatives of naturally occurring naphthalenes
by: Knight, Lorraine Shirley
Published: (2016)

The reactions of substituted naphthalenes with butyl mercaptides
by: South, John Allan
Published: (1972)

Synthesis of Some Heterocyclic Compounds Via Cyclization of Imidoyl Chloride
by: G. T. Sedeek
Published: (2013-10-01)

Photochemical Aryl Radical Cyclizations to Give (E)-3-Ylideneoxindoles
by: Michael Gurry, et al.
Published: (2014-09-01)

Recent Advances in the Synthesis of Thiophene Derivatives by Cyclization of Functionalized Alkynes
by: Raffaella Mancuso, et al.
Published: (2014-09-01)

Structure-Gas Barrier Property Relationship in a Novel Polyimide Containing Naphthalene and Amide Groups: Evaluation by Experiments and Simulations
by: Yi Zeng, et al.
Published: (2021-03-01)

Palladium-catalyzed synthesis and nucleotide pyrophosphatase inhibition of benzo[4,5]furo[3,2-b]indoles
by: Hoang Huy Do, et al.
Published: (2019-11-01)

A New Approach to the Synthesis of Benzo[b]naphtho[2,3-b]furan-6,11-diones and 2-Benzyl-3-hydroxynaphthalene-1,4-diones
by: Jose C. Barcia, et al.
Published: (2017-03-01)

Synthesis of some heterocyclic derivatives of 1,8-Naphthyridine with a new substitution on the Naphthyridine ring
by: Baghdad Science Journal
Published: (2013-09-01)

Recent advances in the electrochemical construction of heterocycles
by: Robert Francke
Published: (2014-12-01)

5-(4-Bromophenyl)-7-(2,4-dimethoxyphenyl)-4,7-dihydrotetrazolo[1,5-<em>a</em>]pyrimidine
by: Kautsar Ul Haq, et al.
Published: (2018-12-01)

Studies on the construction of heterocycles from carbohydrates via intramolecular cyclization.
Published: (1998)

Synthesis of new building blocks for conjugated oligomers
by: Allared, Fredrik
Published: (2004)

Synthesis of 4-amino-5-fluoropyrimidines and 5-amino-4-fluoropyrazoles from a β-fluoroenolate salt
by: Tobias Lucas, et al.
Published: (2020-03-01)