Synthesis, Table of Contents PAPER © Georg Thieme Verlag Stuttgart · New York Synthesis of (Z)-2-(2H-Isoquinolin-1-ylidene)acetamides by Iodine-Mediated Cyclization of (Z)-3-Amino-3-(2-vinylphenyl)propenamides Kazuhiro Kobayashi*, Kenichi Hashimoto, Taiyo Shiokawa, Osamu Morikawa, Hisatoshi KonishiDepartment of Materials Science, Faculty of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, JapanFax: +81(857)315263; e-Mail: kkoba@chem.tottori-u.ac.jp; Recommend Article Abstract Buy Article All articles of this category Abstract (Z)-2-(2-Acetyl-2H-isoquinolin-1-ylidene)acetamides have been synthesized from 2-vinylbenzonitrile derivatives in three steps. The key step involves the iodine-mediated 6-endo cyclization of (Z)-3-acetylamino-3-(2-vinylphenyl)propenamides, which are prepared by the coupling of 2-vinylbenzonitriles with magnesium enolates of tertiary amides followed by N-acetylation. Key words 6-endo cyclization - iodine - isoquinoline - magnesium amide - magnesium enolate Full Text References References 1 Kobayashi K. Miyamoto K. Yamase T. Nakamura D. Morikawa O. Konishi H. Bull. Chem. Soc. Jpn. 2006, 79: 1580 2 Kobayashi K. Miyamoto K. Morikawa O. Konishi H. Bull. Chem. Soc. Jpn. 2005, 78: 886 3 Kobayashi K. Hase M. Hashimoto K. Fujita S. Tanmatsu M. Morikawa O. Konishi H. Synthesis 2006, 2493 For recent reports, see: 4a Konno T. Chae J. Miyabe T. Ishihara T. J. Org. Chem. 2005, 70: 10172 4b Ichikawa J. Sakoda K. Moriyama H. Wada Y. Synthesis 2006, 1590 4c Alonso R. Campos PJ. García B. Rodoríguez MA. Org. Lett. 2006, 8: 3521 For earlier reports, see pertinent references cited in these papers and ref. 9 For recent reports on the biological activity of isoquinoline derivatives: 5a Barber CG. Dickinson RP. Fish PV. Bioorg. Med. Chem. Lett. 2005, 14: 3227 5b Jiang J. Thomas CJ. Neumann S. Lu X. Rice CK. Gershengorn MC. Bioorg. Med. Chem. Lett. 2005, 15: 733 5c Cui W. Iwasa K. Tokuda H. Kashihara A. Mitani Y. Hasegawa T. Nishiyama Y. Moriyasu M. Nishino H. Hanaoka M. Mukai C. Takeda K. Phytochemistry 2006, 67: 70 5d Markmee S. Ruchirawat S. Prachyawarakorn W. Ingkaninan K. Khorana N. Bioorg. Med. Chem. Lett. 2006, 16: 2170 5e Zhu G.-D. Gong J. Claiborne A. Woods KW. Gandhi VB. Thomas S. Luo Y. Liu X. Shi Y. Guan R. Magnone SR. Klinghofer V. Johnson EF. Bouska J. Shoemaker A. Oleksijew A. Stoll VS. De Jong R. Olterdorf T. Li Q. Rosenberg SH. Girranda VL. Bioorg. Med. Chem. Lett. 2006, 16: 3150 A synthesis of (2H-isoquinolin-1-ylidene)acetates by reactions of 2-alkyl-1-methylthioisoquinolinium salts with active methylene compounds has been reported: 6a Fujita R. Watanabe N. Tomisawa H. Chem. Pharm. Bull. 2001, 50: 225 6b Fujita R. Watanabe N. Tomisawa H. Heterocycles 2001, 55: 435 For other reports on the synthesis of related compounds, see: 6c Stanovnik B. Drofenik I. Tisler M. Durst T. Heterocycles 1987, 26: 1805 6d Finke JA. Huisgen R. Temme R. Helv. Chim. Acta 2000, 83: 2363 7a Kobayashi K. Kitamura T. Nakahashi R. Shimizu A. Morikawa O. Konishi H. Heterocycles 2000, 53: 1021 7b Hiyama T. Kobayashi K. Nishide K. Bull. Chem. Soc. Jpn. 1987, 60: 2127 8 Dordor IM. Mellor JM. J. Chem. Soc., Perkin Trans. 1 1984, 1253 9 Kobayashi K. Shiokawa T. Omote H. Hashimoto K. Morikawa O. Konishi H. Bull. Chem. Soc. Jpn. 2006, 79: 1126 10a Helberger JH. von Rebay A. Liebigs Ann. Chem. 1937, 531: 279 10b Alan Aitken R. Fairhurst IM. Ford A. Milne PEY. Russell DW. Whittaker M. J. Chem. Soc., Perkin Trans. 1 1997, 3107 11 Wang S. Morrow GW. Swenton JS. J. Org. Chem. 1989, 54: 5364 12 Peyroux E. Berthiol F. Doucet H. Santelli M. Eur. J. Org. Chem. 2004, 1075