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Literature DB >> 20161270

Synthesis of 2H-chromenes and 1,2-dihydroquinolines from aryl aldehydes, amines, and alkenylboron compounds.

Abstract

The one-step reaction of salicylaldehydes with amines and alkenyl boronic acids or alkenyl trifluoroborates to form 2H-chromenes (2H-1-benzopyrans) has been investigated in more detail and new suitable conditions have been identified, including the use of tertiary amines and protic solvents including water. This process was applied to a concise synthesis of a tocopherol analog. The analogous condensation reaction between 2-sulfamidobenzaldehydes and alkenyl trifluoroborates provides an efficient synthesis of 1,2-dihydroquinoline derivatives.

Entities: Chemical Species

Year: 2009 PMID： 20161270 PMCID： PMC2701707 DOI： 10.1016/j.jorganchem.2008.11.050

Source DB: PubMed Journal: J Organomet Chem ISSN： 0022-328X Impact factor: 2.369

16 in total

1. Palladium-catalyzed enantioselective domino reaction for the efficient synthesis of vitamin E.

Authors: Lutz F Tietze; Konrad M Sommer; Julia Zinngrebe; Florian Stecker
Journal: Angew Chem Int Ed Engl Date: 2004-12-27 Impact factor: 15.336

2. A silver-catalyzed domino route toward 1,2-dihydroquinoline derivatives from simple anilines and alkynes.

Authors: Yumei Luo; Zigang Li; Chao-Jun Li
Journal: Org Lett Date: 2005-06-23 Impact factor: 6.005

3. Chemoenzymatic synthesis of both enantiomers of alpha-tocotrienol.

Authors: Robert Chênevert; Gabriel Courchesne; Nicholas Pelchat
Journal: Bioorg Med Chem Date: 2006-04-17 Impact factor: 3.641

4. Organotrifluoroborates: protected boronic acids that expand the versatility of the Suzuki coupling reaction.

Authors: Gary A Molander; Noel Ellis
Journal: Acc Chem Res Date: 2007-01-26 Impact factor: 22.384

Review 5. Potassium organotrifluoroborates: new perspectives in organic synthesis.

Authors: Sylvain Darses; Jean-Pierre Genet
Journal: Chem Rev Date: 2007-12-21 Impact factor: 60.622

6. Group 3 metal complexes in the preparation of vitamin E.

Authors: P A Wehrli; R I Fryer; W Metlesics
Journal: J Org Chem Date: 1971-09 Impact factor: 4.354

7. 2H-Chromenes from salicylaldehydes by a catalytic petasis reaction

Authors:
Journal: Org Lett Date: 2000-12-14 Impact factor: 6.005

8. Gold(III) chloride-catalyzed three-component reaction: a facile synthesis of alkynyl derivatives of 1,2-dihydroquinolines and isoquinolines.

Authors: Jhillu S Yadav; Basi V Subba Reddy; Nagendra Nath Yadav; Manoj K Gupta; Balasubramanian Sridhar
Journal: J Org Chem Date: 2008-07-29 Impact factor: 4.354

9. Unusual effects in the pd-catalyzed asymmetric allylic alkylations: synthesis of chiral chromans.

Authors: Barry M Trost; Hong C Shen; Li Dong; Jean-Philippe Surivet
Journal: J Am Chem Soc Date: 2003-08-06 Impact factor: 15.419

10. Development of novel antioxidants: design, synthesis, and reactivity.

Authors: Helmi H Hussain; Gordana Babic; Tony Durst; James S Wright; Mihaela Flueraru; Alexandru Chichirau; Leonid L Chepelev
Journal: J Org Chem Date: 2003-09-05 Impact factor: 4.354

11 in total

1. Suzuki-Miyaura cross-coupling of aryl carbamates and sulfamates: experimental and computational studies.

Authors: Kyle W Quasdorf; Aurora Antoft-Finch; Peng Liu; Amanda L Silberstein; Anna Komaromi; Tom Blackburn; Stephen D Ramgren; K N Houk; Victor Snieckus; Neil K Garg
Journal: J Am Chem Soc Date: 2011-04-01 Impact factor: 15.419

2. Simultaneous synthesis of both rings of chromenes via a benzannulation/o-quinone methide formation/electrocyclization cascade.

Authors: Nilanjana Majumdar; Keith A Korthals; William D Wulff
Journal: J Am Chem Soc Date: 2011-12-16 Impact factor: 15.419

Synthesis of 2H-chromenes and 1,2-dihydroquinolines from aryl aldehydes, amines, and alkenylboron compounds.

1. Palladium-catalyzed enantioselective domino reaction for the efficient synthesis of vitamin E.

2. A silver-catalyzed domino route toward 1,2-dihydroquinoline derivatives from simple anilines and alkynes.

3. Chemoenzymatic synthesis of both enantiomers of alpha-tocotrienol.

4. Organotrifluoroborates: protected boronic acids that expand the versatility of the Suzuki coupling reaction.

Review 5. Potassium organotrifluoroborates: new perspectives in organic synthesis.

6. Group 3 metal complexes in the preparation of vitamin E.

7. 2H-Chromenes from salicylaldehydes by a catalytic petasis reaction

8. Gold(III) chloride-catalyzed three-component reaction: a facile synthesis of alkynyl derivatives of 1,2-dihydroquinolines and isoquinolines.

9. Unusual effects in the pd-catalyzed asymmetric allylic alkylations: synthesis of chiral chromans.

10. Development of novel antioxidants: design, synthesis, and reactivity.

1. Suzuki-Miyaura cross-coupling of aryl carbamates and sulfamates: experimental and computational studies.

2. Simultaneous synthesis of both rings of chromenes via a benzannulation/o-quinone methide formation/electrocyclization cascade.

3. Enantioselective addition of boronates to o-quinone methides catalyzed by chiral biphenols.

4. Dimethyl 5,6,7-trimeth-oxy-2-methyl-1,2-dihydro-quinoline-2,4-dicarboxyl-ate.

5. Dimethyl 2-methyl-1,2-dihydro-quinoline-2,4-dicarboxyl-ate.

6. Dimethyl 2,6,8-trimethyl-1,2-dihydroquinoline-2,4-dicarboxylate.

7. Glycerol as an efficient medium for the petasis borono-mannich reaction.

8. Reactions of salicylaldehyde and enolates or their equivalents: versatile synthetic routes to chromane derivatives.

9. Kinetic resolution in asymmetric epoxidation using iminium salt catalysis.

Review 10. Chiral Diol-Based Organocatalysts in Enantioselective Reactions.