Synthesis, Table of Contents PSP© Georg Thieme Verlag Stuttgart · New YorkDirect Synthesis of Substituted Pyrimidines and QuinazolinesMatthew D. Hill, Mohammad Movassaghi*Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USAFax: +1(617)2521504; e-Mail: movassag@mit.edu; Recommend Article Abstract Buy Article All articles of this category Abstract A variety of N-vinyl and N-aryl amides were converted in one step into the corresponding pyrimidine and quinazoline derivatives, respectively. Amide activation with trifluoromethanesulfonic anhydride in the presence of 2-chloropyridine followed by nitrile addition to the activated amide derivative and annulation provides the desired azaheterocycles. Key words amide - nitrile - pyrimidine - quinazoline - annulation Full Text References References Reviews: <A NAME="RZ17607SS-1A">1a</A> Undheim K. Benneche T. In Comprehensive Heterocyclic Chemistry II Vol. 6: Katritzky AR. Rees CW. Scriven EFV. McKillop A. Pergamon; Oxford: 1996. p.93 <A NAME="RZ17607SS-1B">1b</A> Lagoja IM. Chem. Biodiversity 2005, 2: 1 <A NAME="RZ17607SS-1C">1c</A> Michael JP. Nat. Prod. Rep. 2005, 22: 627 <A NAME="RZ17607SS-1D">1d</A> Joule JA. Mills K. In Heterocyclic Chemistry Blackwell Science Ltd.; Cambridge MA: 2000. 4th ed.. p.194 <A NAME="RZ17607SS-1E">1e</A> Erian AW. Chem. Rev. 1993, 93: 1991 For representative reports, see: <A NAME="RZ17607SS-2A">2a</A> Sakai N. Youichi A. Sasada T. Konakahara T. Org. Lett. 2005, 7: 4705 <A NAME="RZ17607SS-2B">2b</A> Yoon DS. Han Y. Stark TM. Haber JC. Gregg BT. Stankovich SB. Org. Lett. 2004, 6: 4775 <A NAME="RZ17607SS-2C">2c</A> Kakiya H. Yagi K. Shinokubo H. Oshima K. J. Am. Chem. Soc. 2002, 124: 9032 <A NAME="RZ17607SS-2D">2d</A> Kotsuki H. Sakai H. Morimoto H. Suenaga H. Synlett 1999, 1993 <A NAME="RZ17607SS-2E">2e</A> Ghosez L. Jnoff E. Bayard P. Sainte F. Beaudegnies R. Tetrahedron 1999, 55: 3387 <A NAME="RZ17607SS-2F">2f</A> Martínez AG. Fernández AH. Fraile AG. Subramanian LR. Hanack M. J. Org. Chem. 1992, 57: 1627 For reviews, see: <A NAME="RZ17607SS-3A">3a</A> Chinchilla R. Nájera C. Yus M. Chem. Rev. 2004, 104: 2667 <A NAME="RZ17607SS-3B">3b</A> Turck A. Plé N. Mongin F. Quéguiner G. Tetrahedron 2001, 57: 4489 <A NAME="RZ17607SS-4">4</A> Movassaghi M. Hill MD. J. Am. Chem. Soc. 2006, 128: 14254 Reviews: <A NAME="RZ17607SS-5A">5a</A> Muci AR. Buchwald SL. Top. Curr. Chem. 2002, 219: 131 <A NAME="RZ17607SS-5B">5b</A> Hartwig JF. In Handbook of Organopalladium Chemistry for Organic Synthesis Negishi E. Wiley-Interscience; New York: 2002. p.1051 <A NAME="RZ17607SS-5C">5c</A> Beletskaya IP. Cheprakov AV. Coord. Chem. Rev. 2004, 248: 2337 <A NAME="RZ17607SS-5D">5d</A> Dehli JR. Legros J. Bolm C. Chem. Commun. 2005, 973 <A NAME="RZ17607SS-6A">6a</A> Movassaghi M. Hill MD. J. Am. Chem. Soc. 2006, 128: 4592 <A NAME="RZ17607SS-6B">6b</A> Hill MD. Movassaghi M. Synthesis 2007, 1115 <A NAME="RZ17607SS-7A">7a</A> Zielinski W. Kudelko A. Monatsh. Chem. 2000, 131: 895 <A NAME="RZ17607SS-7B">7b</A> Kofanov ER. Sosnina VV. Danilova AS. Korolev PV. Zh. Prik. Khim. 1999, 72: 813 ; Russ. J. Appl. Chem. 1999, 72, 850 <A NAME="RZ17607SS-7C">7c</A> Madroñero R. Vega S. Synthesis 1987, 628 <A NAME="RZ17607SS-8">8</A> Bose DS. Jayalakshmi B. Synthesis 1999, 64 <A NAME="RZ17607SS-9">9</A> For a review, see: Baraznenok IL. Nenajdenko VG. Balenkova ES. Tetrahedron 2000, 56: 3077 <A NAME="RZ17607SS-10A">10a</A> Charette AB. Grenon M. Can. J. Chem. 2001, 79: 1694 <A NAME="RZ17607SS-10B">10b</A> Charette AB. Mathieu S. Martel J. Org. Lett. 2005, 7: 5401 <A NAME="RZ17607SS-11A">11a</A> Myers AG. Tom NJ. Fraley ME. Cohen SB. Madar DJ. J. Am. Chem. Soc. 1997, 119: 6072 <A NAME="RZ17607SS-11B">11b</A> Garcia BA. Gin DY. J. Am. Chem. Soc. 2000, 122: 4269