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Literature DB >> 26864495

Efficient one-pot synthesis of 1-arylcycloprop-2-ene-1-carboxamides.

Abstract

An expeditious and cost-efficient method for synthesis of 1-arylcycloprop-2-ene-1-carboxamides was developed. This one-pot protocol involving coupling of amines with acyl chlorides, generated upon treatment of cyclopenylcarboxylic acids with oxalyl chloride, is applicable for the preparation of sensitive products with a reactive, unsubstituted strained double bond.

Entities: CellLine Chemical Disease Species

Mesh：

Substances：
Amides
Carboxylic Acids

Year: 2016 PMID： 26864495 PMCID： PMC4876632 DOI： 10.1039/c6ob00156d

Source DB: PubMed Journal: Org Biomol Chem ISSN： 1477-0520 Impact factor: 3.876

18 in total

1. Catalytic enantioselective hydrostannation of cyclopropenes.

Authors: Marina Rubina; Michael Rubin; Vladimir Gevorgyan
Journal: J Am Chem Soc Date: 2004-03-31 Impact factor: 15.419

2. Indium-catalyzed cycloisomerizations of cyclopropene-3,3-dicarbonyl compounds: efficient access to benzo-fused heteroaromatics and heterobiaryls.

Authors: Lien H Phun; Joel Aponte-Guzman; Stefan France
Journal: Angew Chem Int Ed Engl Date: 2012-02-16 Impact factor: 15.336

3. Studies on the stability of cycloprop-2-ene carboxylate dianions and reactions with electrophiles.

Authors: Laural A Fisher; Joseph M Fox
Journal: J Org Chem Date: 2008-10-14 Impact factor: 4.354

4. Isomeric cyclopropenes exhibit unique bioorthogonal reactivities.

Authors: David N Kamber; Lidia A Nazarova; Yong Liang; Steven A Lopez; David M Patterson; Hui-Wen Shih; K N Houk; Jennifer A Prescher
Journal: J Am Chem Soc Date: 2013-09-06 Impact factor: 15.419

5. Genetically encoded cyclopropene directs rapid, photoclick-chemistry-mediated protein labeling in mammalian cells.

Authors: Zhipeng Yu; Yanchao Pan; Zhiyong Wang; Jiangyun Wang; Qing Lin
Journal: Angew Chem Int Ed Engl Date: 2012-09-20 Impact factor: 15.336

6. Diastereoselectivity control in formal nucleophilic substitution of bromocyclopropanes with oxygen- and sulfur-based nucleophiles.

Authors: Joseph E Banning; Anthony R Prosser; Bassam K Alnasleh; Jason Smarker; Marina Rubina; Michael Rubin
Journal: J Org Chem Date: 2011-04-14 Impact factor: 4.354

2. Synthesis of novel indole-isoxazole hybrids and evaluation of their cytotoxic activities on hepatocellular carcinoma cell lines.

Authors: Mohammed Hawash; Deniz Cansen Kahraman; Sezen Guntekin Ergun; Rengul Cetin-Atalay; Sultan Nacak Baytas
Journal: BMC Chem Date: 2021-12-20

2 in total

Efficient one-pot synthesis of 1-arylcycloprop-2-ene-1-carboxamides.

1. Catalytic enantioselective hydrostannation of cyclopropenes.

2. Indium-catalyzed cycloisomerizations of cyclopropene-3,3-dicarbonyl compounds: efficient access to benzo-fused heteroaromatics and heterobiaryls.

3. Studies on the stability of cycloprop-2-ene carboxylate dianions and reactions with electrophiles.

4. Isomeric cyclopropenes exhibit unique bioorthogonal reactivities.

5. Genetically encoded cyclopropene directs rapid, photoclick-chemistry-mediated protein labeling in mammalian cells.

6. Diastereoselectivity control in formal nucleophilic substitution of bromocyclopropanes with oxygen- and sulfur-based nucleophiles.

7. Catalytic enantioselective hydroboration of cyclopropenes.

8. Functionalized cyclopropenes as bioorthogonal chemical reporters.

9. Palladium-catalyzed hydrophosphorylation and hydrophosphinylation of cyclopropenes.

10. One-pot synthesis of GABA amides via the nucleophilic addition of amines to 3,3-disubstituted cyclopropenes.

1. Directed nucleophilic addition of phenoxides to cyclopropenes.

2. Synthesis of novel indole-isoxazole hybrids and evaluation of their cytotoxic activities on hepatocellular carcinoma cell lines.