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Literature DB >> 26049825

Copper-catalyzed ligand-free amidation of aryl iodides and amino acid amides to synthesize C3-(Z)-1H-benzo[e][1,4]diazepin-2(3H)-ones.

Abstract

An effective synthetic method for C3-chiral 1,4-benzodiazepine-2-ones is described in this paper, reporting good yields and high enantioselectivity with a novel approach to an ipso-halo displacement-cyclization benzodiazepine route.

Entities: Chemical

Keywords: Amidation; C3-(Z)-1H-benzo[e][1, 4]diazepin-2(3H)-ones; Copper-catalyzed; Cyclization; Diazepinones

Mesh：

Substances：

Year: 2015 PMID： 26049825 DOI： 10.1007/s11030-015-9603-5

Source DB: PubMed Journal: Mol Divers ISSN： 1381-1991 Impact factor: 2.943

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References

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Authors: Artis Klapars; Sean Parris; Kevin W Anderson; Stephen L Buchwald
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Copper-catalyzed ligand-free amidation of aryl iodides and amino acid amides to synthesize C3-(Z)-1H-benzo[e][1,4]diazepin-2(3H)-ones.

1. Identification and structure-activity studies of novel ultrashort-acting benzodiazepine receptor agonists.

2. Novel 1,4-benzodiazepine derivatives with antiproliferative properties on tumor cell lines.

Review 3. Copper-mediated coupling reactions and their applications in natural products and designed biomolecules synthesis.

4. Combinatorial solid phase synthesis of multiply substituted 1,4-benzodiazepines and affinity studies on the CCK2 receptor (part 1).

5. Palladium- and copper-catalyzed synthesis of medium- and large-sized ring-fused dihydroazaphenanthrenes and 1,4-benzodiazepine-2,5-diones. control of reaction pathway by metal-switching.

6. Rapid approach to 3,5-disubstituted 1,4-benzodiazepines via the photo-fries rearrangement of anilides.

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8. Copper/amino acid catalyzed cross-couplings of aryl and vinyl halides with nucleophiles.

9. A general and efficient copper catalyst for the amidation of aryl halides.

10. Synthesis of medium ring nitrogen heterocycles via a tandem copper-catalyzed C-N bond formation-ring-expansion process.