Cart
Letter
Cu-Catalyzed Tandem C−N Bond Formation for the Synthesis of Pyrroles and Heteroarylpyrroles
Full Text HTML
Hi-Res PDFPurchase the full-text
- PDF/HTML,
figures/images,
references and tables,
(where available)
Abstract
A highly efficient Cu-catalyzed tandem C−N bond-forming reaction of 1,4-dihalo-1,3-dienes has been developed. The transformation allows the synthesis of pyrroles and heteroarylpyrroles with a wide variety of functional groups and substitution patterns from readily available precursors.
Citing Articles
Citation data is made available by participants in CrossRef's Cited-by Linking service. For a more comprehensive list of citations to this article, users are encouraged to perform a search in SciFinder.
This article has been cited by 29 ACS Journal articles (5 most recent appear below).
Sequential C–N and C–O Bond Formation in a Single Pot: Synthesis of 2H-Benzo[b][1,4]oxazines from 2,5-Dihydroxybenzaldehyde and Amino acid Precursors
Javed Iqbal, Neelima D. Tangellamudi, Balakrishna Dulla, and Sridhar BalasubramanianOrganic Letters2012 14 (2), 552-555Sequential C–N and C–O Bond Formation in a Single Pot: Synthesis of 2H-Benzo[b][1,4]oxazines from 2,5-Dihydroxybenzaldehyde and Amino acid Precursors
Javed Iqbal, Neelima D. Tangellamudi, Balakrishna Dulla, and Sridhar BalasubramanianOrganic Letters2012 14 (2), 552-555Functionalized β-aryl alanine ester derivatives were found to undergo rapid C–N and C–O bond formation with quinol carbonyl compounds to afford 2H-benzo[b][1,4]oxazines in good to excellent yields. This unprecedented finding reported herein offers a ...
Three-Component Synthesis of Polysubstituted Pyrroles from α-Diazoketones, Nitroalkenes, and Amines
Deng Hong, Yuanxun Zhu, Yao Li, Xufeng Lin, Ping Lu, and Yanguang WangOrganic Letters2011 Article ASAPThree-Component Synthesis of Polysubstituted Pyrroles from α-Diazoketones, Nitroalkenes, and Amines
Deng Hong, Yuanxun Zhu, Yao Li, Xufeng Lin, Ping Lu, and Yanguang WangOrganic Letters2011 Article ASAPPolysubstituted pyrroles are regiospecifically synthesized via the copper-catalyzed three-component reaction of α-diazoketones, nitroalkenes, and amines under aerobic conditions. The cascade process involves an N–H insertion of carbene, a copper-catalyzed ...
Synthesis of Substituted 1,4,5,6-Tetrahydrocyclopenta[b]pyrroles by Platinum-Catalyzed Cascade Cyclization/Ring Expansion of 2-Alkynyl-1-Azaspiro[2.3]hexanes
Masahiro Yoshida , Yohei Maeyama , Mohammad Al-Amin , and Kozo ShishidoThe Journal of Organic Chemistry 0 (ja),Synthesis of Substituted 1,4,5,6-Tetrahydrocyclopenta[b]pyrroles by Platinum-Catalyzed Cascade Cyclization/Ring Expansion of 2-Alkynyl-1-Azaspiro[2.3]hexanes
Masahiro Yoshida , Yohei Maeyama , Mohammad Al-Amin , and Kozo ShishidoThe Journal of Organic Chemistry 0 (ja),The reaction of 2-alkynyl-1-azaspiro[2.3]hexanes with a platinum catalyst is described. 1,4,5,6-Tetrahydrocyclopenta[b]pyrroles having a variety of substituents were conveniently synthesized via a cascade cyclization/ring expansion process.
Palladium-Catalyzed Synthesis of Benzosilolo[2,3-b]indoles via Cleavage of a C(sp3)–Si Bond and Consequent Intramolecular C(sp2)–Si Coupling
Yun Liang, Shaoguang Zhang, and Zhenfeng XiJournal of the American Chemical Society2011 Article ASAPPalladium-Catalyzed Synthesis of Benzosilolo[2,3-b]indoles via Cleavage of a C(sp3)–Si Bond and Consequent Intramolecular C(sp2)–Si Coupling
Yun Liang, Shaoguang Zhang, and Zhenfeng XiJournal of the American Chemical Society2011 Article ASAPAn efficient process involving Pd-catalyzed selective cleavage of a C(sp3)–Si bond and consequent intramolecular C(sp2)–Si coupling has been developed, affording benzosilolo[2,3-b]indoles as a new type of silicon-bridged polyheteroarene in excellent ...
One-Pot Synthesis of 1,2-Dihydropyridines: Expanding the Diverse Reactivity of Propargyl Vinyl Ethers
Tobias Harschneck and Stefan F. KirschThe Journal of Organic Chemistry2011 76 (7), 2145-2156One-Pot Synthesis of 1,2-Dihydropyridines: Expanding the Diverse Reactivity of Propargyl Vinyl Ethers
Tobias Harschneck and Stefan F. KirschThe Journal of Organic Chemistry2011 76 (7), 2145-2156The catalyzed synthesis of 1,2-dihydropyridines starting from easily accessible propargyl vinyl ethers was realized. The reaction sequence involving a transition metal-catalyzed propargyl-Claisen rearrangement, a condensation step, and a Brønsted acid-...
Tools
-
Add to Favorites
-
Download Citation
-
Email a Colleague -
Permalink
Order Reprints
Rights & Permissions
Citation Alerts
History
- Published In Issue August 16, 2007
- Received June 18, 2007
ACS
Network
Facebook
Tweet This
CiteULike
Newsvine
Digg This
Delicious
