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Literature DB >> 21443189

Why do some Fischer indolizations fail?

Nihan Çelebi-Ölçüm¹, Ben W Boal, Alexander D Huters, Neil K Garg, K N Houk.

Abstract

The mechanisms of the Fischer indole synthesis and competing cleavage pathways were explored with SCS-MP2/6-31G(d) and aqueous solvation calculations. Electron-donating substituents divert the reaction pathway to heterolytic N-N bond cleavage and preclude the acid-promoted [3,3]-sigmatropic rearrangement.

Entities: Chemical Gene

Mesh：

Substances：
Indoles
indole

Year: 2011 PMID： 21443189 PMCID： PMC3076556 DOI： 10.1021/ja201035b

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

18 in total

1. Total synthesis of kapakahine E and F.

Authors: Vinson R Espejo; Jon D Rainier
Journal: Org Lett Date: 2010-05-07 Impact factor: 6.005

Review 2. Practical methodologies for the synthesis of indoles.

Authors: Guy R Humphrey; Jeffrey T Kuethe
Journal: Chem Rev Date: 2006-07 Impact factor: 60.622

3. Enantiospecific total syntheses of kapakahines B and F.

Authors: Timothy Newhouse; Chad A Lewis; Phil S Baran
Journal: J Am Chem Soc Date: 2009-05-13 Impact factor: 15.419

4. An interrupted Fischer indolization approach toward fused indoline-containing natural products.

Authors: Ben W Boal; Alex W Schammel; Neil K Garg
Journal: Org Lett Date: 2009-08-06 Impact factor: 6.005

5. New synthesis of benzo-delta-carbolines, cryptolepines, and their salts: in vitro cytotoxic, antiplasmodial, and antitrypanosomal activities of delta-carbolines, benzo-delta-carbolines, and cryptolepines.

Authors: E Arzel; P Rocca; P Grellier; M Labaeïd; F Frappier; F Guéritte; C Gaspard; F Marsais; A Godard; G Quéguiner
Journal: J Med Chem Date: 2001-03-15 Impact factor: 7.446

6. First total synthesis of trimeric indole alkaloid, psychotrimine.

Authors: Yohei Matsuda; Mariko Kitajima; Hiromitsu Takayama
Journal: Org Lett Date: 2007-12-11 Impact factor: 6.005

7. Total synthesis of chaetominine.

Authors: Mathieu Toumi; François Couty; Jérome Marrot; Gwilherm Evano
Journal: Org Lett Date: 2008-10-11 Impact factor: 6.005

8. [Pyrido [3,2-b]indol-4-yl-amines--synthesis and investigation of activity against malaria].

Authors: K Görlitzer; C Kramer; H Meyer; R D Walter; H Jomaa; J Wiesner
Journal: Pharmazie Date: 2004-04 Impact factor: 1.267

9. Total synthesis of (+/-)-psychotrimine.

Authors: Timothy Newhouse; Phil S Baran
Journal: J Am Chem Soc Date: 2008-07-26 Impact factor: 15.419

10. An expeditious synthesis of C(3)-N(1') heterodimeric indolines.

Authors: Vinson R Espejo; Jon D Rainier
Journal: J Am Chem Soc Date: 2008-09-06 Impact factor: 15.419

7 in total

1. Pericyclic cascade with chirality transfer: reaction pathway and origin of enantioselectivity of the hetero-Claisen approach to oxindoles.

Authors: Nihan Çelebi-Ölçüm; Yu-hong Lam; Edward Richmond; Kenneth B Ling; Andrew D Smith; Kendall N Houk
Journal: Angew Chem Int Ed Engl Date: 2011-10-04 Impact factor: 15.336

2. Pardon the Interruption: A Modification of Fischer's Venerable Reaction for the Synthesis of Heterocycles and Natural Products.

Authors: Robert B Susick; Lucas A Morrill; Elias Picazo; Neil K Garg
Journal: Synlett Date: 2017 Impact factor: 2.454