Preparation and Synthetic Use of Polymer-Supported Acetoacetate Reagent

Takeshi Hirai; Hideo Togo

doi:10.1055/s-2005-872142

PAPER

Preparation and Synthetic Use of Polymer-Supported Acetoacetate Reagent

Takeshi Hirai^a, Hideo Togo*^a,b
^a Graduate School of Science and Technology, Chiba University, Yayoi-cho 1-33, Inage-ku 263-8522, Chiba, Japan
^b Department of Chemistry, Faculty of Science, Chiba University, Yayoi-cho 1-33, Inage-ku 263-8522, Chiba, Japan
Fax: +81(43)2902874; e-Mail: togo@faculty.chiba-u.jp;

Abstract

All articles of this category

Abstract

Coumarin synthesis using polymer-supported acetoacetate reagent was carried out to produce various coumarin derivatives in excellent yield and purity with a facile work-up process. It was found that the polymer reagent could be recycled without any diminishment of the yield and purity.

Key words

polymer-supported acetoacetate - coumarin - Knoevenagel condensation - von Pechmann reaction - green chemistry

Full Text

References

<A NAME="RF05605SS-1A">1a</A> Donnelly DMX. Meegan MJ. Comp. Heterocycl. Chem. 1984, 4: 685

<A NAME="RF05605SS-1B">1b</A> Sundberg RT. Comp. Heterocycl. Chem. 1984, 4: 344

<A NAME="RF05605SS-1C">1c</A> Fisher H. Org. Synth. Col. Vol. 2 Wiley; New York: 1943. p.202

<A NAME="RF05605SS-1D">1d</A> Cheng CC. Yan SJ. Org. React. 1982, 28: 37

<A NAME="RF05605SS-1E">1e</A> Lauer WM. Kaslow CE. Org. Synth. Col. Vol. 3 Wiley; New York: 1955. p.580

<A NAME="RF05605SS-1F">1f</A> Jones G. Comp. Heterocycl. Chem. 1984, 2: 426

<A NAME="RF05605SS-1G">1g</A> Biginelli P. Gazz. Chim. Ital. 1893, 23: 360

Recent work:

<A NAME="RF05605SS-2A">2a</A> Tracey MR. Hsung RP. Lambeth RH. Synthesis 2004, 827

<A NAME="RF05605SS-2B">2b</A> Boehme TM. Augelli-Szafran CE. Hallak H. Schwarz RD. Med. Chem. Res. 2002, 11: 423

<A NAME="RF05605SS-2C">2c</A> Hayakawa I. Shinomiya R. Agatsuma T. Furukawa H. Naruto S. Sugano B. Med. Chem. Lett. 2004, 14: 4383

<A NAME="RF05605SS-2D">2d</A> Lyle MPA. Wilson PD. Org. Lett. 2004, 6: 855

<A NAME="RF05605SS-2E">2e</A> Chung C.-P. Wu Y.-L. Tetrahedron 2004, 60: 1841

<A NAME="RF05605SS-2F">2f</A> Fu N.-Y. Yuan Y.-F. Pang M.-L. Wang J.-T. Peppe C. J. Organomet. Chem. 2003, 672: 52

Reviews:

<A NAME="RF05605SS-3A">3a</A> Kirschning A. Monenschein H. Wittenberg R. Angew. Chem. Int. Ed. 2001, 40: 650

<A NAME="RF05605SS-3B">3b</A> Bhalay G. Dunstan A. Glen A. Synlett 2000, 1846

<A NAME="RF05605SS-3C">3c</A> Sakuratani K. Togo H. Synlett 2002, 1966

<A NAME="RF05605SS-3D">3d</A> Drewry DH. Coe DM. Poon S. Med. Res. Rev. 1999, 19: 97

<A NAME="RF05605SS-4A">4a</A> Chen J.-M. Huang X. Synthesis 2004, 1577

<A NAME="RF05605SS-4B">4b</A> Ueno M. Nabana T. Togo H. J. Org. Chem. 2003, 68: 6424

<A NAME="RF05605SS-4C">4c</A> Sakuratani K. Togo H. Synthesis 2003, 21

<A NAME="RF05605SS-4D">4d</A> Ley SV. Thomas AW. Finch H. J. Chem. Soc., Perkin Trans. 1 1999, 669

<A NAME="RF05605SS-4E">4e</A> Crosignani S. White PD. Linclau B. J. Org. Chem. 2004, 69: 5897

<A NAME="RF05605SS-4F">4f</A> Petricci E. Mugnaini C. Radi M. Corelli F. Botta M. J. Org. Chem. 2004, 69: 7880

<A NAME="RF05605SS-4G">4g</A> Gerlach M. Joerdens F. Kuhn H. Neumann WP. Peterseim M. J. Org. Chem. 1991, 56: 5971

Related polymer-supported reagents:

<A NAME="RF05605SS-5A">5a</A> Watson BT. Christiansen GE. Tetrahedron Lett. 1998, 39: 6087

<A NAME="RF05605SS-5B">5b</A> Van Eynde JJ. Rutot D. Tetrahedron 1999, 55: 2687

<A NAME="RF05605SS-6A">6a</A> Palmer CJ. Josephs JL. J. Chem. Soc., Perkin Trans. 1 1995, 3135

<A NAME="RF05605SS-6B">6b</A> Costova IN. Nikolov NM. Chipilska LN. J. Ethnopharm. 1993, 39: 205

<A NAME="RF05605SS-6C">6c</A> Wang CL. Hsieh YJ. Chu CY. Lin YL. Tseng TH. Cancer Lett. 2002, 183: 163

<A NAME="RF05605SS-6D">6d</A> Mitra AK. De A. Karchaudhuri N. Misra SK. Mukhopadhyay AK. J. Indian Chem. Soc. 1998, 75: 666

<A NAME="RF05605SS-7A">7a</A> Clemens RJ. Hyatt JA. J. Org. Chem. 1985, 50: 2431

<A NAME="RF05605SS-7B">7b</A> Clemens RJ. Witzeman JS. J. Am. Chem. Soc. 1989, 111: 2186

<A NAME="RF05605SS-8A">8a</A> Knoevenagel E. Ber. Dtsch. Chem. Ges. 1896, 29: 172

<A NAME="RF05605SS-8B">8b</A> Jones G. Org. React. 1967, 15: 204

<A NAME="RF05605SS-8C">8c</A> Green B. Crane RI. Khaidem IS. Leighton RS. Newaz SS. Smyser TE. J. Org. Chem. 1985, 50: 640

<A NAME="RF05605SS-8D">8d</A> Su C. Chen Z.-C. Zheng Q.-G. Synthesis 2003, 555

<A NAME="RF05605SS-8E">8e</A> Bigi F. Chesini L. Maggi R. Sartori G. J. Org. Chem. 1999, 64: 1033

<A NAME="RF05605SS-9">9</A> Sugino T. Tanaka K. Chem. Lett. 2001, 30: 110

<A NAME="RF05605SS-10A">10a</A> von Pechmann H. Duisberg C. Ber. Dtsch. Chem. Ges. 1883, 16: 2119

<A NAME="RF05605SS-10B">10b</A> Sethna S. Phadke R. Org. React. 1953, 7: 1 ; and references cited therein

<A NAME="RF05605SS-10C">10c</A> Woodruff EH. Org. Synth. Col. Vol. 3 Wiley; New York: 1965. p.581

<A NAME="RF05605SS-10D">10d</A> Miyano M. Dorn CR. J. Org. Chem. 1972, 37: 259

<A NAME="RF05605SS-10E">10e</A> Brun M.-P. Bischoff L. Garbay C. Angew. Chem. Int. Ed. 2004, 43: 3432

<A NAME="RF05605SS-11A">11a</A> John EVO. Israelstam SS. J. Org. Chem. 1961, 26: 240

<A NAME="RF05605SS-11B">11b</A> de la Hoz A. Moreno A. Vazquez E. Synlett 1999, 608

<A NAME="RF05605SS-11C">11c</A> Bose DS. Rudradas AP. Babu MH. Tetrahedron Lett. 2002, 43: 9195

<A NAME="RF05605SS-11D">11d</A> Singh PR. Singh DU. Samant SD. Synlett 2004, 1909

<A NAME="RF05605SS-12">12</A> Nishiguchi T. Hayakawa S. Hirasaka Y. Saitoh M. Tetrahedron Lett. 2000, 41: 9843

<A NAME="RF05605SS-13">13</A> Bao W. Wang Z. Li Y. J. Chem. Res., Synop. 2003, 294

<A NAME="RF05605SS-14">14</A> Rajyalakshmi K. Srinivasan VR. J. Heterocycl. Chem. 1980, 17: 1737

<A NAME="RF05605SS-15">15</A> Czerney P. Hartmann H. J. Prakt. Chem. 1982, 324: 21

<A NAME="RF05605SS-16">16</A> Fontaine L. Therapie 1968, 23: 359

<A NAME="RF05605SS-17">17</A> Trost BM. Toste FD. Greenman K. J. Am. Chem. Soc. 2003, 125: 4518