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Literature DB >> 12762706

The first method for protection-deprotection of the indole 2,3-pi bond.

Phil S Baran¹, Carlos A Guerrero, E J Corey.

Abstract

[reaction: see text] The scope and generality of a new reaction of indoles with MTAD is discussed. In most cases the ene-type reaction proceeds within seconds or minutes at 0 degrees C to provide the urazole adducts in high yield. This reaction provides the first method for protecting the indole 2,3-double bond since the urazole adducts can be reconverted to the starting indole (retro-ene) simply by heating.

Entities: Chemical

Mesh：

Substances：

Year: 2003 PMID： 12762706 DOI： 10.1021/ol034634x

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

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Cited

10 in total

1. Triazolinediones enable ultrafast and reversible click chemistry for the design of dynamic polymer systems.

Authors: Stijn Billiet; Kevin De Bruycker; Frank Driessen; Hannelore Goossens; Veronique Van Speybroeck; Johan M Winne; Filip E Du Prez
Journal: Nat Chem Date: 2014-08-11 Impact factor: 24.427

2. Straightforward Access to Hexahydropyrrolo[2,3-b]indole Core by a Regioselective C3-Azo Coupling Reaction of Arenediazonium Compounds with Tryptamines.

Authors: David E Stephens; Oleg V Larionov
Journal: European J Org Chem Date: 2014-06-01

3. Scalable Total Syntheses of (-)-Hapalindole U and (+)-Ambiguine H.

Authors: Thomas J Maimone; Yoshihiro Ishihara; Phil S Baran
Journal: Tetrahedron Date: 2015-05-02 Impact factor: 2.457

4. Triazolinedione protein modification: from an overlooked off-target effect to a tryptophan-based bioconjugation strategy.

Authors: Klaas W Decoene; Kamil Unal; An Staes; Olivier Zwaenepoel; Jan Gettemans; Kris Gevaert; Johan M Winne; Annemieke Madder
Journal: Chem Sci Date: 2022-03-15 Impact factor: 9.969

The first method for protection-deprotection of the indole 2,3-pi bond.

1. Triazolinediones enable ultrafast and reversible click chemistry for the design of dynamic polymer systems.

2. Straightforward Access to Hexahydropyrrolo[2,3-b]indole Core by a Regioselective C3-Azo Coupling Reaction of Arenediazonium Compounds with Tryptamines.

3. Scalable Total Syntheses of (-)-Hapalindole U and (+)-Ambiguine H.

4. Triazolinedione protein modification: from an overlooked off-target effect to a tryptophan-based bioconjugation strategy.

5. Facile and stabile linkages through tyrosine: bioconjugation strategies with the tyrosine-click reaction.

6. Concise total synthesis of (+)-asperazine A and (+)-pestalazine B.

7. Development of a Scalable and Sublimation-Free Route to MTAD.

8. Design of a thermally controlled sequence of triazolinedione-based click and transclick reactions.

9. On the prevalence of bridged macrocyclic pyrroloindolines formed in regiodivergent alkylations of tryptophan.

10. Exploiting Urazole's Acidity for Fabrication of Hydrogels and Ion-Exchange Materials.