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Literature DB >> 21556391

Decarboxylative formation of N-alkyl pyrroles from 4-hydroxyproline.

Indubhusan Deb¹, Daniel J Coiro, Daniel Seidel.

Abstract

N-Alkyl pyrroles are obtained in a single step from 4-hydroxyproline and aldehydes in just 15 min under microwave irradiation. This journal is © The Royal Society of Chemistry 2011

Entities: Chemical

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Year: 2011 PMID： 21556391 DOI： 10.1039/c1cc11560j

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

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Cited

10 in total

1. Facile Access to Ring-Fused Aminals via Direct α-Amination of Secondary Amines with ortho-Aminobenzaldehydes. Synthesis of Vasicine, Deoxyvasicine, Deoxyvasicinone, Mackinazolinone and Ruteacarpine.

Authors: Matthew T Richers; Indubhusan Deb; Alena Yu Platonova; Chen Zhang; Daniel Seidel
Journal: Synthesis (Stuttg) Date: 2013-10-06 Impact factor: 3.157

2. Redox-neutral α-C-H bond functionalization of secondary amines with concurrent C-P bond formation/N-alkylation.

Authors: Deepankar Das; Daniel Seidel
Journal: Org Lett Date: 2013-08-19 Impact factor: 6.005

3. Decarboxylative Annulation of α-Amino Acids with β-Ketoaldehydes.

Authors: Anirudra Paul; N R Thimmegowda; Thiago Galani Cruz; Daniel Seidel
Journal: Org Lett Date: 2018-01-12 Impact factor: 6.005

4. Suzuki-Miyaura cross-coupling of potassium trifluoro(N-methylheteroaryl)borates with aryl and heteroaryl halides.

Authors: Gary A Molander; DaWeon Ryu; Mona Hosseini-Sarvari; Rammohan Devulapally; Dave G Seapy
Journal: J Org Chem Date: 2013-06-25 Impact factor: 4.354

5. Redox-neutral copper(II) carboxylate catalyzed α-alkynylation of amines.

Authors: Deepankar Das; Aaron X Sun; Daniel Seidel
Journal: Angew Chem Int Ed Engl Date: 2013-02-25 Impact factor: 15.336

6. Metal-free α-amination of secondary amines: computational and experimental evidence for azaquinone methide and azomethine ylide intermediates.

Authors: Arne Dieckmann; Matthew T Richers; Alena Yu Platonova; Chen Zhang; Daniel Seidel; K N Houk
Journal: J Org Chem Date: 2013-04-02 Impact factor: 4.354

Decarboxylative formation of N-alkyl pyrroles from 4-hydroxyproline.

1. Facile Access to Ring-Fused Aminals via Direct α-Amination of Secondary Amines with ortho-Aminobenzaldehydes. Synthesis of Vasicine, Deoxyvasicine, Deoxyvasicinone, Mackinazolinone and Ruteacarpine.

2. Redox-neutral α-C-H bond functionalization of secondary amines with concurrent C-P bond formation/N-alkylation.

3. Decarboxylative Annulation of α-Amino Acids with β-Ketoaldehydes.

4. Suzuki-Miyaura cross-coupling of potassium trifluoro(N-methylheteroaryl)borates with aryl and heteroaryl halides.

5. Redox-neutral copper(II) carboxylate catalyzed α-alkynylation of amines.

6. Metal-free α-amination of secondary amines: computational and experimental evidence for azaquinone methide and azomethine ylide intermediates.

7. Dual C-H functionalization of N-aryl amines: synthesis of polycyclic amines via an oxidative Povarov approach.

8. Redox-neutral α-oxygenation of amines: reaction development and elucidation of the mechanism.

9. Redox-neutral α-sulfenylation of secondary amines: ring-fused N,S-acetals.

10. Decarboxylative Annulation of α-Amino Acids with γ-Nitroaldehydes.