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Literature DB >> 24910496

CYCLOADDITION REACTIONS OF AZIDE, FURAN, AND PYRROLE UNITS WITH BENZYNES GENERATED BY THE HEXADEHYDRO-DIELS-ALDER (HDDA) REACTION.

Junhua Chen¹, Beeraiah Baire¹, Thomas R Hoye¹.

Abstract

Benzynes can be generated by the intramolecular thermal cycloisomerization of triynes-the title HDDA reaction. We report here that these can be trapped by cycloaddition reaction with trimethylsilyl azide (1,3-dipolar) or a furan or pyrrole (4+2 Diels-Alder).

Entities: CellLine Chemical Disease Gene

Year: 2014 PMID： 24910496 PMCID： PMC4045115 DOI： 10.3987/COM-13-S(S)83

Source DB: PubMed Journal: Heterocycles ISSN： 0385-5414 Impact factor: 0.831

12 in total

Review 1. A comprehensive history of arynes in natural product total synthesis.

Authors: Pamela M Tadross; Brian M Stoltz
Journal: Chem Rev Date: 2012-03-23 Impact factor: 60.622

2. Arynes and cyclohexyne in natural product synthesis.

Authors: Christian M Gampe; Erick M Carreira
Journal: Angew Chem Int Ed Engl Date: 2012-03-15 Impact factor: 15.336

3. Synthesis of complex benzenoids via the intermediate generation of o-benzynes through the hexadehydro-Diels-Alder reaction.

Authors: Beeraiah Baire; Dawen Niu; Patrick H Willoughby; Brian P Woods; Thomas R Hoye
Journal: Nat Protoc Date: 2013-02-14 Impact factor: 13.491

4. Concerted vs stepwise mechanisms in dehydro-Diels-Alder reactions.

Authors: Aida Ajaz; Alexander Z Bradley; Richard C Burrell; William Hoi Hong Li; Kimberly J Daoust; Laura Boddington Bovee; Kenneth J DiRico; Richard P Johnson
Journal: J Org Chem Date: 2011-10-18 Impact factor: 4.354

5. Amino acid derived heterocycles: lewis acid catalyzed and radical cyclizations from peptide acetals.

Authors: Matthew H Todd; Chudi Ndubaku; Paul A Bartlett
Journal: J Org Chem Date: 2002-06-14 Impact factor: 4.354

6. Single-crystal-to-single-crystal topochemical polymerizations of a terminal diacetylene: two remarkable transformations give the same conjugated polymer.

Authors: Xi Ouyang; Frank W Fowler; Joseph W Lauher
Journal: J Am Chem Soc Date: 2003-10-15 Impact factor: 15.419

7. Use of benzynes for the synthesis of heterocycles.

Authors: Anton V Dubrovskiy; Nataliya A Markina; Richard C Larock
Journal: Org Biomol Chem Date: 2012-11-06 Impact factor: 3.876

8. The hexadehydro-Diels-Alder reaction.

Authors: Thomas R Hoye; Beeraiah Baire; Dawen Niu; Patrick H Willoughby; Brian P Woods
Journal: Nature Date: 2012-10-11 Impact factor: 49.962

9. Synthesis of natural-product-like molecules with over eighty distinct scaffolds.

Authors: Daniel Morton; Stuart Leach; Christopher Cordier; Stuart Warriner; Adam Nelson
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

10. Alkane desaturation by concerted double hydrogen atom transfer to benzyne.

Authors: Dawen Niu; Patrick H Willoughby; Brian P Woods; Beeraiah Baire; Thomas R Hoye
Journal: Nature Date: 2013-09-26 Impact factor: 49.962

9 in total

1. Reactions of Diaziridines with Benzynes Give N-Arylhydrazones.

Authors: Sahil Arora; Vignesh Palani; Thomas R Hoye
Journal: Org Lett Date: 2018-12-11 Impact factor: 6.005

2. Hexadehydro-Diels-Alder (HDDA)-Enabled Carbazolyne Chemistry: Single Step, de Novo Construction of the Pyranocarbazole Core of Alkaloids of the Murraya koenigii (Curry Tree) Family.

Authors: Tao Wang; Thomas R Hoye
Journal: J Am Chem Soc Date: 2016-10-13 Impact factor: 15.419

9. The domino hexadehydro-Diels-Alder reaction transforms polyynes to benzynes to naphthynes to anthracynes to tetracynes (and beyond?).

Authors: Xiao Xiao; Thomas R Hoye
Journal: Nat Chem Date: 2018-07-20 Impact factor: 24.427