Synthesis of Substituted Pyridines and Quinolines

Matthew D. Hill; Mohammad Movassaghi

doi:10.1055/s-2007-965940

PSP

Synthesis of Substituted Pyridines and Quinolines

Matthew D. Hill, Mohammad Movassaghi*
Department of Chemistry, Massachusettes Institute of Technology, Cambridge, MA 02139, USA
Fax: +1(617)2521504; e-Mail: movassag@mit.edu;

Abstract

All articles of this category

Abstract

A variety of N-vinyl and N-aryl amides were converted to the corresponding pyridine and quinoline derivatives, respectively. Amide activation and nucleophilic addition of copper(I) (trimethylsilyl)acetylide efficiently provided the desired alkynyl imines. Ruthenium-catalyzed protodesilylation and cycloisomerization of these imines gave the corresponding azaheterocycles.

Key words

amide - imine - pyridine - quinoline - vinylidene

Full Text

References

Reviews:

<A NAME="RZ24206SS-1A">1a</A> Henry GD. Tetrahedron 2004, 60: 6043

<A NAME="RZ24206SS-1B">1b</A> Michael JP. Nat. Prod. Rep. 2005, 22: 627

<A NAME="RZ24206SS-1C">1c</A> Abass M. Heterocycles 2005, 65: 901

<A NAME="RZ24206SS-2A">2a</A> Jones G. In Comprehensive Heterocyclic Chemistry II Vol. 5: Katritzky AR. Rees CW. Scriven EFV. McKillop A. Pergamon; Oxford: 1996. p.167

<A NAME="RZ24206SS-2B">2b</A> Larock RC. Comprehensive Organic Transformations: A Guide to Functional Group Preparations Wiley-VCH; New York: 1999.

Reviews:

<A NAME="RZ24206SS-3A">3a</A> Boger DL. Chem. Rev. 1986, 86: 781

<A NAME="RZ24206SS-3B">3b</A> Bönnemann H. Brijoux W. Adv. Heterocycl. Chem. 1990, 48: 177

<A NAME="RZ24206SS-3C">3c</A> Boger DL. J. Heterocycl. Chem. 1998, 35: 1003

<A NAME="RZ24206SS-3D">3d</A> Jayakumar S. Ishar MPS. Mahajan MP. Tetrahedron 2002, 58: 379

<A NAME="RZ24206SS-3E">3e</A> Nakamura I. Yamamoto Y. Chem. Rev. 2004, 104: 2127

<A NAME="RZ24206SS-3F">3f</A> Zeni G. Larock RC. Chem. Rev. 2004, 104: 2285

<A NAME="RZ24206SS-3G">3g</A> Varela JA. Saá C. Chem. Rev. 2004, 104: 3787

Representative related reports:

<A NAME="RZ24206SS-4A">4a</A> Roesch KR. Larock RC. Org. Lett. 1999, 1: 553

<A NAME="RZ24206SS-4B">4b</A> Varela JA. Castedo L. Saá C. J. Org. Chem. 2003, 68: 8595

<A NAME="RZ24206SS-4C">4c</A> Sangu K. Fuchibe K. Akiyama T. Org. Lett. 2004, 6: 353

<A NAME="RZ24206SS-4D">4d</A> Zhang X. Campo MA. Yao T. Larock RC. Org. Lett. 2005, 7: 763

<A NAME="RZ24206SS-4E">4e</A> McCormick MM. Duong HA. Zuo G. Louie J. J. Am. Chem. Soc. 2005, 127: 5030 ; and references cited therein

Reviews:

<A NAME="RZ24206SS-5A">5a</A> Chinchilla R. Nájera C. Yus M. Chem. Rev. 2004, 104: 2667

<A NAME="RZ24206SS-5B">5b</A> Turck A. Plé N. Mongin F. Quéguiner G. Tetrahedron 2001, 57: 4489

<A NAME="RZ24206SS-6">6</A> Movassaghi M. Hill MD. J. Am. Chem. Soc. 2006, 128: 4592

Reviews:

<A NAME="RZ24206SS-7A">7a</A> Muci AR. Buchwald SL. Top. Curr. Chem. 2002, 219: 131

<A NAME="RZ24206SS-7B">7b</A> Hartwig JF. In Handbook of Organopalladium Chemistry for Organic Synthesis Negishi E. Wiley-Interscience; New York: 2002. p.1051

<A NAME="RZ24206SS-7C">7c</A> Beletskaya IP. Cheprakov AV. Coord. Chem. Rev. 2004, 248: 2337

<A NAME="RZ24206SS-7D">7d</A> Dehli JR. Legros J. Bolm C. Chem. Commun. 2005, 973

Examples:

<A NAME="RZ24206SS-8A">8a</A> Ried W. Erle H.-E. Chem. Ber. 1979, 112: 640

<A NAME="RZ24206SS-8B">8b</A> Austin WB. Bilow N. Kelleghan WJ. Lau KSY. J. Org. Chem. 1981, 46: 2280

<A NAME="RZ24206SS-8C">8c</A> Lin S.-Y. Sheng H.-Y. Huang Y.-Z. Synthesis 1991, 235

For related reports, see:

<A NAME="RZ24206SS-8D">8d</A> Kel’in AV. Sromek AW. Gevorgyan V. J. Am. Chem. Soc. 2001, 123: 2074

<A NAME="RZ24206SS-8E">8e</A> Van den Hoven BG. Alper H. J. Am. Chem. Soc. 2001, 123: 10214

<A NAME="RZ24206SS-9">9</A> Review: Baraznenok IL. Nenajdenko VG. Balenkova ES. Tetrahedron 2000, 56: 3077

Examples:

<A NAME="RZ24206SS-10A">10a</A> Charette AB. Grenon M. Can. J. Chem. 2001, 79: 1694

<A NAME="RZ24206SS-10B">10b</A> Charette AB. Mathieu S. Martel J. Org. Lett. 2005, 7: 5401

Examples:

<A NAME="RZ24206SS-11A">11a</A> Myers AG. Tom NJ. Fraley ME. Cohen SB. Madar DJ. J. Am. Chem. Soc. 1997, 119: 6072

<A NAME="RZ24206SS-11B">11b</A> Garcia BA. Gin DY. J. Am. Chem. Soc. 2000, 122: 4269

<A NAME="RZ24206SS-11C">11c</A> Movassaghi M. Hill MD. J. Am. Chem. Soc. 2006, 128: 14254

<A NAME="RZ24206SS-12A">12a</A> Gilbert JD. Wilkinson G. J. Chem. Soc. A 1969, 1749

<A NAME="RZ24206SS-12B">12b</A> Blackmore T. Bruce MI. Stone FGA. J. Chem. Soc. A 1971, 2376

<A NAME="RZ24206SS-12C">12c</A> Bruce MI. Windsor NJ. Aust. J. Chem. 1977, 30: 1601

<A NAME="RZ24206SS-13">13</A> Walker SD. Barder TE. Martinelli JR. Buchwald SL. Angew. Chem. Int. Ed. 2004, 43: 1871