Inverse Electron Demand Diels-Alder Reactions of Heterodienes Catalyzed by Potassium Hydrogen Sulfate: Diastereoselective, One-Pot Synthesis of Pyranobenzopyrans, Furanobenzopyrans and Tetrahydroquinolines Derivatives

R. Senthil Kumar; Rajagopal Nagarajan; Paramasivan T. Perumal

doi:10.1055/s-2004-822332

PAPER

Inverse Electron Demand Diels-Alder Reactions of Heterodienes Catalyzed by Potassium Hydrogen Sulfate: Diastereoselective, One-Pot Synthesis of Pyranobenzopyrans, Furanobenzopyrans and Tetrahydroquinolines Derivatives

R. Senthil Kumar, Rajagopal Nagarajan, Paramasivan T. Perumal*
Organic Chemistry Division, Central Leather Research Institute, Adyar, Chennai - 600 020, India
Fax: +91(44)24911589; e-Mail: ptperumal@hotmail.com;

Abstract

Alle Artikel dieser Rubrik

Abstract

Potassium hydrogen sulfate catalyzes the one-pot three components coupling of aldehydes, anilines, and electron rich dienophiles such as dihydropyran, dihydrofuran, ethyl vinylether, and cyclopentadiene. With o-hydroxybenzaldehyde, the reaction probably proceeds through the formation of o-quinonemethide intermediate, which subsequently undergoes cycloaddition with cyclic and acyclic enol ethers leading to the formation of respective chromanes. However, in case of benzaldehydes with no o-hydroxy group, the imine formed acts as the heterodiene and leads to the formation of tetrahydroquinolines.

Keywords

heterodienes - potassium hydrogen sulfate - pyranobenzopyrans - furanobenzopyrans - tetrahydroquinolines

Volltext

Referenzen

References

<A NAME="RZ15903SS-1A">1a</A> Schweizer EE. Meeder-Nycz O. In Chromenes Chromanes Chromones Ellis GP. Wiley-Inter-science; New York: 1977. p.11-139

<A NAME="RZ15903SS-1B">1b</A> Bowers WS. Ohta T. Cleere JS. Marsella PA. Science 1976, 193: 542

<A NAME="RZ15903SS-2">2</A> Hepworth J. Comprehensive Heterocyclic Chemistry Vol. 3: Katritzky AR. Rees CW. Pergamon; Oxford: 1984. p.737

<A NAME="RZ15903SS-3A">3a</A> Rovnyak GC. Ahmed SZ. Ding CZ. Dzwonczyk S. Ferrara FN. Humphreys WG. Grover GJ. Santafinos D. Atwal KS. Baird AJ. McLaughin LG. Normandin DE. Sleph PG. Traeger SC. J. Med. Chem. 1997, 40: 24

<A NAME="RZ15903SS-3B">3b</A> Evans JM. Fake CS. Hamilton TC. Poyser RH. Watts EA. J. Med. Chem. 1983, 26: 1582

<A NAME="RZ15903SS-3C">3c</A> Buckle DR. Arch JRS. Fenwick AE. Hough-Frydrych CSV. Pinto IL. Smith DG. Taylor SG. Tedder . J. Med. Chem. 1990, 33: 3028

<A NAME="RZ15903SS-4">4</A> Perry NB. Blunt JW. McCombs JD. Munro MHG. J.Org.Chem. 1986, 51: 5476

<A NAME="RZ15903SS-5">5</A> Perry NB. Blunt JW. Munro MHG. Tetrahedron 1988, 44: 1727

<A NAME="RZ15903SS-6">6</A> Perry NB. Blunt JW. Munro MHG. Sakai R. J. Org. Chem. 1988, 53: 4127

<A NAME="RZ15903SS-7">7</A> Konishi M. Zercher CK. Bechkam S. Haubold E.-M. J. Am. Chem. Soc. 1990, 112: 3715

<A NAME="RZ15903SS-8">8</A> Wender PA. Zercher CK. Bechkam S. Haubold E.-M. J. Org. Chem. 1993, 58: 5867

<A NAME="RZ15903SS-9">9</A> Uchida M. Chihiro M. Morita S. Kanbe T. Yamashita H. Yamasakai K. Yabuuchi Y. Nakagawa K. Chem. Pharm. Bull. 1989, 37: 2109

<A NAME="RZ15903SS-10">10</A> Miller KE. Huang C.-T. Portlock DE. Wright GC. Life Sci. 1987, 40: 63

<A NAME="RZ15903SS-11">11</A> Atwal K. inventors; Eur. Pat. EP 488,616.

<A NAME="RZ15903SS-12">12</A> Carling RW. Leeson PD. Mosely AM. Smith JD. Saywell K. Tricklebank MD. Kemp JA. Marshal GR. Foster AC. Grimwood S. Bioorg. Med. Chem. Lett. 1993, 3: 65

<A NAME="RZ15903SS-13">13</A> Tsushima K. Osumi T. Matsuo N. Itaya N. Agricult. Biol. Chem. 1989, 53: 2529

<A NAME="RZ15903SS-14">14</A> Evans S. inventors; Eur. Pat. EP 497,735.

<A NAME="RZ15903SS-15">15</A> Shikhaliev KhS. Shmyreva ZhV. Gurova EM. Izv.Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol. 1989, 32: 85

<A NAME="RZ15903SS-16">16</A> Ramesh M. Mohan PA. Shanmugam P. Tetrahedron 1984, 40: 4041

<A NAME="RZ15903SS-17">17</A> Nesterova IN. Alekseeva LM. Andreeva LM. Andreeva NI. Golovira SM. Granic VG. Khim.-Farm. Zh. 1995, 29: 31 ; Chem. Abstr. 1996, 128, 117128

<A NAME="RZ15903SS-18">18</A> Yamada N. Kadowaki S. Takahashi K. Umezu K. Biochem. Pharmacol. 1992, 44: 1211

<A NAME="RZ15903SS-19">19</A> Faber K. Stueckler H. Kappe T. J. Heterocycl. Chem. 1984, 21: 1177

<A NAME="RZ15903SS-20">20</A> Akhmed Khodzhaeva KS. Bessonova IA. Dokl. Akad. Nauk Uzh. SSR 1982, 34 ; Chem. Abstr., 1983, 98: 83727

<A NAME="RZ15903SS-21A">21a</A> Jurd L. Wong RV. Aust. J. Chem. 1981, 34: 1625

<A NAME="RZ15903SS-21B">21b</A> Coppola GM. J. Heterocycl. Chem. 1983, 20: 1217

<A NAME="RZ15903SS-22">22</A> Wildman WC. Alkaloids 1960, 6: 289 ; and references therein

<A NAME="RZ15903SS-23">23</A> Lucchini V. Prato M. Scorrano G. Tecilla P. J. Org. Chem. 1998, 53: 2251

<A NAME="RZ15903SS-24">24</A> Miyazaki H. Honda K. Asami M. Inhouse S. J. Org. Chem. 1999, 64: 9507

<A NAME="RZ15903SS-25">25</A> Ma Y. Qian C. Xie M. Sun J. J. Org. Chem. 1999, 64: 6462

<A NAME="RZ15903SS-26">26</A> Grieco PA. Bahsas A. Tetrahedron Lett. 1998, 29: 5855