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Literature DB >> 21394235

[2+2] Cycloaddition of ketenes with ynamides. A general method for the synthesis of 3-aminocyclobutenone derivatives.

Amanda L Kohnen¹, Xiao Yin Mak, Tin Yiu Lam, Joshua R Dunetz, Rick L Danheiser.

Abstract

Ynamides react with ketenes in [2+2] cycloadditions leading to a variety of substituted 3-aminocyclobut-2-en-1-ones. The ynamides employed in these reactions are readily available via the copper-promoted N-alkynylation of carbamates and sulfonamides with alkynyl bromides and iodides. The scope of the [2+2] cycloaddition with regard to both the ketene and ynamide component is described.

Entities: Chemical

Year: 2006 PMID： 21394235 PMCID： PMC3050601 DOI： 10.1016/j.tet.2005.11.088

Source DB: PubMed Journal: Tetrahedron ISSN： 0040-4020 Impact factor: 2.457

8 in total

1. Total synthesis of (-)-ascochlorin via a cyclobutenone-based benzannulation strategy.

Authors: G B Dudley; K S Takaki; D D Cha; R L Danheiser
Journal: Org Lett Date: 2000-10-19 Impact factor: 6.005

2. The application of cyclobutane derivatives in organic synthesis.

Authors: Jan C Namyslo; Dieter E Kaufmann
Journal: Chem Rev Date: 2003-04 Impact factor: 60.622

3. Ruthenium-catalyzed [2 + 2] cycloadditions of ynamides.

Authors: Nicole Riddell; Karine Villeneuve; William Tam
Journal: Org Lett Date: 2005-08-18 Impact factor: 6.005

4. Rhodium-catalyzed rearrangement of alpha-diazo thiol esters to thio-substituted ketenes. Application in the synthesis of cyclobutanones, cyclobutenones, and beta-lactams.

Authors: M D Lawlor; T W Lee; R L Danheiser
Journal: J Org Chem Date: 2000-07-14 Impact factor: 4.354

5. A copper-catalyzed C-N bond formation involving sp-hybridized carbons. A direct entry to chiral ynamides via N-alkynylation of amides.

Authors: Michael O Frederick; Jason A Mulder; Michael R Tracey; Richard P Hsung; Jian Huang; Kimberly C M Kurtz; Lichun Shen; Christopher J Douglas
Journal: J Am Chem Soc Date: 2003-03-05 Impact factor: 15.419

6. Efficient synthesis of 3-aminocyclobut-2-en-1-ones: squaramide surrogates as potent VLA-4 antagonists.

Authors: Stephen Brand; Benjamin C de Candole; Julien A Brown
Journal: Org Lett Date: 2003-06-26 Impact factor: 6.005

7. Copper-mediated N-alkynylation of carbamates, ureas, and sulfonamides. A general method for the synthesis of ynamides.

Authors: Joshua R Dunetz; Rick L Danheiser
Journal: Org Lett Date: 2003-10-16 Impact factor: 6.005

8. Copper sulfate-pentahydrate-1,10-phenanthroline catalyzed amidations of alkynyl bromides. Synthesis of heteroaromatic amine substituted ynamides.

Authors: Yanshi Zhang; Richard P Hsung; Michael R Tracey; Kimberly C M Kurtz; Eymi L Vera
Journal: Org Lett Date: 2004-04-01 Impact factor: 6.005

8 in total

9 in total

Review 1. Ynamides: a modern functional group for the new millennium.

Authors: Kyle A DeKorver; Hongyan Li; Andrew G Lohse; Ryuji Hayashi; Zhenjie Lu; Yu Zhang; Richard P Hsung
Journal: Chem Rev Date: 2010-09-08 Impact factor: 60.622

2. Catalytic intramolecular decarbonylative coupling of 3-aminocyclobutenones and alkenes: a unique approach to [3.1.0] bicycles.

Authors: Xuan Zhou; Imran Zafar; Guangbin Dong
Journal: Tetrahedron Date: 2015-07-01 Impact factor: 2.457

3. Batch and flow photochemical benzannulations based on the reaction of ynamides and diazo ketones. Application to the synthesis of polycyclic aromatic and heteroaromatic compounds.

Authors: Thomas P Willumstad; Olesya Haze; Xiao Yin Mak; Tin Yiu Lam; Yu-Pu Wang; Rick L Danheiser
Journal: J Org Chem Date: 2013-10-28 Impact factor: 4.354

4. A Concise Total Synthesis of Dictyodendrins F, H, and I Using Aryl Ynol Ethers as Key Building Blocks.

Authors: Wenhan Zhang; Joseph M Ready
Journal: J Am Chem Soc Date: 2016-08-11 Impact factor: 15.419

5. SYNTHESIS OF YNAMIDES BY N-ALKYNYLATION OF AMINE DERIVATIVES. PREPARATION OF N-ALLYL-N-(METHOXYCARBONYL)-1,3-DECADIYNYLAMINE.

Authors: Amanda L Kohnen; Joshua R Dunetz; Rick L Danheiser
Journal: Organic Synth Date: 2007

6. Synthesis of polycyclic benzofused nitrogen heterocycles via a tandem ynamide benzannulation/ring-closing metathesis strategy. Application in a formal total synthesis of (+)-FR900482.

Authors: Xiao Yin Mak; Aimee L Crombie; Rick L Danheiser
Journal: J Org Chem Date: 2011-02-15 Impact factor: 4.354