A Practical Preparation of Highly Versatile N-Acylpyrroles from 2,4,4-Trimethoxybutan-1-amine

Tomoaki Maehara, Rentaro Kanno, Satoshi Yokoshima, and Tohru Fukuyama*

Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan

Org. Lett., 2012, 14 (7), pp 1946–1948

DOI: 10.1021/ol3005613

Publication Date (Web): March 26, 2012

fukuyama@mol.f.u-tokyo.ac.jp

Abstract

A novel method for the preparation of N-acylpyrrole is described. The method involves condensation of carboxylic acids with 2,4,4-trimethoxybutan-1-amine, followed by acid-mediated cyclization to form the pyrrole ring. The preparative procedure is highly tolerant of a variety of functional groups.

Supporting Information

Experimental details and ¹H and ¹³C NMR spectra for all new compounds. This material is available free of charge via the Internet at http://pubs.acs.org.

View: ACS ActiveView PDF | PDF | PDF w/ Links | Full Text HTML

Applications of Convertible Isonitriles in the Ligation and Macrocyclization of Multicomponent Reaction-Derived Peptides and Depsipeptides

Ludger A. Wessjohann, Micjel C. Morejón, Gerardo M. Ojeda, Cristiano R. B. Rhoden, and Daniel G. Rivera

The Journal of Organic Chemistry 2016 81 (15), 6535-6545

Metrics

Letter

A Practical Preparation of Highly Versatile N-Acylpyrroles from 2,4,4-Trimethoxybutan-1-amine

Abstract

Supporting Information

PDF

Proofs

Applications of Convertible Isonitriles in the Ligation and Macrocyclization of Multicomponent Reaction-Derived Peptides and Depsipeptides

An Efficient Chemoenzymatic Synthesis of Coenzyme A and Its Disulfide

Synthesis of Peramine, an Anti-insect Defensive Alkaloid Produced by Endophytic Fungi of Cool Season Grasses

Synthesis, Reactions and Uses of Isocyanides in Organic Synthesis. An Update

Convertible Isocyanides: Application in Small Molecule Synthesis, Carbohydrate Synthesis, and Drug Discovery

Brønsted acid-promoted synthesis of common heterocycles and related bio-active and functional molecules

Rhodium/bisphosphine-thiourea-catalyzed enantioselective hydrogenation of α,β-unsaturated N-acylpyrazoles

One-pot synthesis of alkyl pyrrole-2-carboxylates starting from β-nitroacrylates and primary amines

Silver acetate-assisted formation of amides from acyl chlorides

Pyrrole: a resourceful small molecule in key medicinal hetero-aromatics

Regiospecific Synthesis of 7-Hydroxyindoles from Pyrroles by Anionic Benzannulation

Protection for the Carboxyl Group

A mild and efficient AgSbF6-catalyzed synthesis of fully substituted pyrroles through a sequential propargylation/amination/cycloisomerization reaction

Nano Sulfated Titania as a Heterogeneous Solid Acid Catalyst for the Synthesis of Pyrroles by Clauson–Kaas Condensation under Solvent-free Conditions

One-pot metal-free synthesis of highly substituted pyrroles from 2-acetyl-3-methylene-1,4-dicarbonyl compounds and primary amines via TBHP and activated carbon oxidative aromatization of dihydropyrrole

A Cationic High-Valent Cp*Co III Complex for the Catalytic Generation of Nucleophilic Organometallic Species: Directed CH Bond Activation

A Cationic High-Valent Cp*Co III Complex for the Catalytic Generation of Nucleophilic Organometallic Species: Directed CH Bond Activation

Five-Membered Ring Systems

4-Isocyanopermethylbutane-1,1,3-triol (IPB): a convertible isonitrile for multicomponent reactions

ChemInform Abstract: A Practical Preparation of Highly Versatile N-Acylpyrroles from 2,4,4-Trimethoxybutan-1-amine.

Other ACS content by these authors:

Related Content:

Metrics

Products

User Resources

Support

Partners

Letter

A Practical Preparation of Highly Versatile N-Acylpyrroles from 2,4,4-Trimethoxybutan-1-amine

Abstract

PDF

Proofs

Other ACS content by these authors:

Related Content:

Metrics

Explore by:

Products

User Resources

Support

Partners