Sequential Ugi reaction/base-induced ring closing/IAAC protocol toward triazolobenzodiazepine-fused diketopiperazines and hydantoins

Sequential Ugi reaction/base-induced ring closing/IAAC protocol toward triazolobenzodiazepine-fused diketopiperazines and hydantoins

A practical three-step protocol for the assembly of triazolobenzodiazepine-fused diketopiperazines and hydantoins has been developed. The synthesis of these tetracyclic ring systems was initiated by an Ugi reaction, which brought together all necessary functionalities for further transformations. Th...

Full description

Bibliographic Details
Main Authors:	Robby Vroemans, Fante Bamba, Jonas Winters, Joice Thomas, Jeroen Jacobs, Luc Van Meervelt, Jubi John, Wim Dehaen
Format:	Article
Language:	English
Published:	Beilstein-Institut 2018-03-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	benzodiazepine 2,5-diketopiperazine hydantoin intramolecular azide–alkyne cycloaddition Ugi reaction
Online Access:	https://doi.org/10.3762/bjoc.14.49

Similar Items

One-Pot Ugi/Aza-Michael Synthesis of Highly Substituted 2,5-Diketopiperazines with Anti-Proliferative Properties
by: Ulrike Holzgrabe, et al.
Published: (2012-12-01)

Post-Ugi gold-catalyzed diastereoselective domino cyclization for the synthesis of diversely substituted spiroindolines
by: Amit Kumar, et al.
Published: (2013-10-01)

Studies in the Hydantoin Series. III. 5-(2-Pyridyl)Hydantoin and its Derivatives
by: Carter, Johnny Sherman
Published: (1959)

Studies in the Hydantoin Series. II. 5-(3-Pyridyl)hydantoin and Its Derivatives
by: Banta, Marion Calvin
Published: (1957)

Hydantoins as Anticonvulsants. III. 5-Alkoxy- and Aryloxymethyl-5-(2-Thienyl) Hydantoins
by: Sadler, Jack W.
Published: (1950)

Consecutive hydrazino-Ugi-azide reactions: synthesis of acylhydrazines bearing 1,5-disubstituted tetrazoles
by: Angélica de Fátima S. Barreto, et al.
Published: (2017-12-01)

Studies in the Hydantoin Series. I. 5-(4-pyridyl)hydantoin and Its Detrivatives
by: Crowe, Robert E.
Published: (1957)

Hydantoins as Anticonvulsants. IV. The Synthesis of 5-Substituted-5-(2-Tetrahydropyranyl) Hydantoins
by: Toothaker, Wallis Lee
Published: (1950)

Multi-Gram Synthesis of Enantiopure 1,5-Disubstituted Tetrazoles Via Ugi-Azide 3-Component Reaction
by: Pietro Capurro, et al.
Published: (2018-10-01)

Hydantoins as Anticonvulsants. VI. 5-Substituted-Alkoxy Derivatives of 5-Phenylhydantoin
by: Hoffman, James Rucker
Published: (1954)

Synthesis of 5,5-diphenyl-3-(methylthiomethyl)hydantoin and 5,5-diphenyl-3-(methysulfonylomethyl)hydantoin
by: Barbara Szpakiewicz, et al.
Published: (2006-03-01)

Hydantoins as Anticonvulsants. V. 5-Substituted-Amino Derivatives of 5-Phenylhydantoin
by: Jeanes, Dewey Perry
Published: (1950)

Hydantoin Derivatives as Anticonvulsants. I. 5-Cyclohexylalkyl-5-(2-Thienyl)Hydantoins
by: Baker, Andy Albert
Published: (1949)

Hydantoins as Anticonvulsants. VI. 5-Substituted-Mercapto Derivatives of 5-Phenylhydantoin
by: Wiist, Herbert A.
Published: (1951)

Hydantoins as Anticonvulsants. IX. 5-Alkylideniminoxy Derivatives of 5-Phenylhydantoin
by: Shoulders, Ben Allen
Published: (1957)

Synthesis of hydantoin and thiohydantoin related compounds from benzil and study of their cytotoxicity
by: A. Kashem Liton and M. Rabiul Islam
Published: (2006-06-01)

Synthesis of hydantoin and thiohydantoin related compounds from benzil and study of their cytotoxicity
by: A. Kashem Liton, et al.
Published: (2006-06-01)

Synthesis of hydantoin and thiohydantoin related compounds from benzil and study of their cytotoxicity
by: A Kashem Liton, et al.
Published: (2006-03-01)

Characterization of the hydantoin-hydrolysing system of Pseudomonas putida RU-KM3s
by: Matcher, Gwynneth Felicity
Published: (2005)

Synthesis of 1,5-Disubstituted Tetrazoles in Aqueous Micelles at Room Temperature
by: Mohammed Abdessalam, et al.
Published: (2021-03-01)

DFT Studies on the Stereoselective Three-Component Ugi Reaction
by: Elaheh Sadat Sharifzadeh, et al.
Published: (2019-03-01)

Synthesis and Activity of Novel Acylthiourea with Hydantoin
by: Mingan Wang, et al.
Published: (2013-09-01)

Post-Ugi Cyclization for the Construction of Diverse Heterocyclic Compounds: Recent Updates
by: Jitender Bariwal, et al.
Published: (2018-11-01)

Hydantoins as Anticonvulsants. VIII. 5-Alkylmercapto Derivatives of 3-Methyl-5-Phenylhydantoin
by: Dick, Clarence Reinhardt
Published: (1954)

Tandem Cu-catalyzed ketenimine formation and intramolecular nucleophile capture: Synthesis of 1,2-dihydro-2-iminoquinolines from 1-(o-acetamidophenyl)propargyl alcohols
by: Gadi Ranjith Kumar, et al.
Published: (2014-05-01)

A STUDY OF THE BEHAVIOR AND LOCALIZATION OF PT(II) AZIDE AND ALKYNE-MODIFIED DERIVATIVES IN CELLS USING BIOORTHOGONAL CHEMISTRY AND FLUORESCENCE MICROSCOPY
by: Moghaddam, Alan
Published: (2016)

Isolation, expression and purification of the hydantoin hydrolysing enzymes of agrobacterium tumefaciens
by: Clark, Sally-Ann
Published: (2003)

A facile synthesis of cysteine-based diketopiperazine from thiol-protected precursor
by: Di Zhang, et al.
Published: (2018-01-01)

Enhancement of mechanical property of modified polyurethane with bis-butyl succinate
by: Thi Sinh VO, et al.
Published: (2021-05-01)

Antinociceptive Effect of Hydantoin 3-Phenyl-5-(4-ethylphenyl)-imidazolidine-2,4-dione in Mice
by: Ronaldo Bezerra de Queiroz, et al.
Published: (2015-01-01)

A New Prenylated Indole Diketopiperazine Alkaloid from Eurotium cristatum
by: Xianwei Zou, et al.
Published: (2014-11-01)

The Bucherer–Bergs Multicomponent Synthesis of Hydantoins—Excellence in Simplicity
by: Martin Kalník, et al.
Published: (2021-06-01)

Synthesis and characterization by infrared spectroscopy of hydantoin-based bonding agents, used in composite propellants
by: Darci C. Pires, et al.
Published: (2009-06-01)

Raising the Diversity of Ugi Reactions Through Selective Alkylations and Allylations of Ugi Adducts
by: Alaa Zidan, et al.
Published: (2019-01-01)

Hydantoins as Anticonvulsants. VII. 5-Substituted-Aryloxy Derivatives of 5-Phenylhydantoin
by: Griffin, Margurite Oleva
Published: (1953)

Understanding the complexity of metabolic regulatory systems an investigation into the regulation of hydantoin-hydrolysis in Pseudomonas putida RU-KM3s
by: De la Mare, Jo-Anne
Published: (2009)

A mechanochemical approach to access the proline–proline diketopiperazine framework
by: Nicolas Pétry, et al.
Published: (2017-10-01)

Isolation and Structure Identification of Novel Brominated Diketopiperazines from Nocardia ignorata—A Lichen-Associated Actinobacterium
by: Alba Noël, et al.
Published: (2017-02-01)

Synthesis of Novel bis-1,5-Disubstituted-1H-Tetrazoles by an Efficient Catalyst-Free Ugi-Azide Repetitive Process
by: Luís E. Cárdenas-Galindo, et al.
Published: (2015-01-01)

Two New Indolyl Diketopiperazines, Trypostatins C and D from Aspergillus penicilliodes Speg.
by: Han Zhang, et al.
Published: (2018-03-01)