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Literature DB >> 21446677

Synthesis of saturated 1,4-benzodiazepines via Pd-catalyzed carboamination reactions.

Joshua D Neukom¹, Alvin S Aquino, John P Wolfe.

Abstract

A new synthesis of 1,4-benzodiazepines and 1,4-benzodiazepin-5-ones is reported. The Pd-catalyzed coupling of N-allyl-2-aminobenzylamine derivatives with aryl bromides affords the heterocyclic products in good yield, and substrates bearing allylic methyl groups are transformed to cis-2,3-disubstituted products with >20:1 dr.

Entities: Chemical Disease Gene

Mesh：

Substances：
Benzodiazepines
Palladium

Year: 2011 PMID： 21446677 PMCID： PMC3084890 DOI： 10.1021/ol200429a

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

30 in total

Review 1. BMS-214662 (Bristol-Myers Squibb).

Authors: Stephen R D Johnston
Journal: IDrugs Date: 2003-01

2. Palladium-catalyzed alkene carboamination reactions for the synthesis of substituted piperazines.

Authors: Josephine S Nakhla; Danielle M Schultz; John P Wolfe
Journal: Tetrahedron Date: 2009-09-15 Impact factor: 2.457

3. The enantioselective intramolecular aminative functionalization of unactivated alkenes, dienes, allenes and alkynes for the synthesis of chiral nitrogen heterocycles.

Authors: Sherry R Chemler
Journal: Org Biomol Chem Date: 2009 Impact factor: 3.876

4. Selective synthesis of 5- or 6-aryl octahydrocyclopenta[b]pyrroles from a common precursor through control of competing pathways in a Pd-catalyzed reaction.

Authors: Joshua E Ney; John P Wolfe
Journal: J Am Chem Soc Date: 2005-06-22 Impact factor: 15.419

5. Pd-catalyzed carboamination of oxazolidin-2-ones: a stereoselective route to trans-2,5-disubstituted pyrrolidines.

Authors: Georgia S Lemen; John P Wolfe
Journal: Org Lett Date: 2010-05-21 Impact factor: 6.005

6. Homogeneous gold-catalyzed oxidative carboheterofunctionalization of alkenes.

Authors: Guozhu Zhang; Li Cui; Yanzhao Wang; Liming Zhang
Journal: J Am Chem Soc Date: 2010-02-10 Impact factor: 15.419

7. Palladium-catalyzed synthesis of N-aryl pyrrolidines from gamma-(N-Arylamino) alkenes: evidence for chemoselective alkene insertion into Pd--N bonds.

Authors: Joshua E Ney; John P Wolfe
Journal: Angew Chem Int Ed Engl Date: 2004-07-05 Impact factor: 15.336

8. Mild conditions for Pd-catalyzed carboamination of N-protected hex-4-enylamines and 1-, 3-, and 4-substituted pent-4-enylamines. Scope, limitations, and mechanism of pyrrolidine formation.

Authors: Myra Beaudoin Bertrand; Joshua D Neukom; John P Wolfe
Journal: J Org Chem Date: 2008-10-23 Impact factor: 4.354

4. Metal-free synthesis of 1,4-benzodiazepines and quinazolinones from hexafluoroisopropyl 2-aminobenzoates at room temperature.

Authors: Jiewen Chen; En Liang; Jie Shi; Yinrong Wu; Kangmei Wen; Xingang Yao; Xiaodong Tang
Journal: RSC Adv Date: 2021-01-28 Impact factor: 3.361

4 in total

Synthesis of saturated 1,4-benzodiazepines via Pd-catalyzed carboamination reactions.

Review 1. BMS-214662 (Bristol-Myers Squibb).

2. Palladium-catalyzed alkene carboamination reactions for the synthesis of substituted piperazines.

3. The enantioselective intramolecular aminative functionalization of unactivated alkenes, dienes, allenes and alkynes for the synthesis of chiral nitrogen heterocycles.

4. Selective synthesis of 5- or 6-aryl octahydrocyclopenta[b]pyrroles from a common precursor through control of competing pathways in a Pd-catalyzed reaction.

5. Pd-catalyzed carboamination of oxazolidin-2-ones: a stereoselective route to trans-2,5-disubstituted pyrrolidines.

6. Homogeneous gold-catalyzed oxidative carboheterofunctionalization of alkenes.

7. Palladium-catalyzed synthesis of N-aryl pyrrolidines from gamma-(N-Arylamino) alkenes: evidence for chemoselective alkene insertion into Pd--N bonds.

8. Mild conditions for Pd-catalyzed carboamination of N-protected hex-4-enylamines and 1-, 3-, and 4-substituted pent-4-enylamines. Scope, limitations, and mechanism of pyrrolidine formation.

9. Hydrazides as tunable reagents for alkene hydroamination and aminocarbonylation.

10. Palladium-catalyzed carboamination of alkenes promoted by N-fluorobenzenesulfonimide via C-H activation of arenes.

1. SnAP reagents for the one-step synthesis of medium-ring saturated N-heterocycles from aldehydes.

2. Copper-promoted synthesis of 1,4-benzodiazepinones via alkene diamination.

3. Recent Developments in Pd-Catalyzed Alkene Aminoarylation Reactions for the Synthesis of Nitrogen Heterocycles.

4. Metal-free synthesis of 1,4-benzodiazepines and quinazolinones from hexafluoroisopropyl 2-aminobenzoates at room temperature.