2-Acylpyridazin-3-ones: Novel Mild and Chemoselective Acylating Agents for Amines

Young-Jin Kang; Hyun-A. Chung; Jeum-Jong Kim; Yong-Jin Yoon

doi:10.1055/s-2002-25760

PAPER

2-Acylpyridazin-3-ones: Novel Mild and Chemoselective Acylating Agents for Amines

Young-Jin Kang, Hyun-A Chung, Jeum-Jong Kim, Yong-Jin Yoon*
Department of Chemistry and Research Institute of Natural Sciences, Gyeongsang National University, Chinju 660-701, Korea
Fax: +82(55)7610244; e-Mail: yjyoon@nongae.gsnu.ac.kr;

Abstract

All articles of this category

Abstract

2-Acyl-4,5-dichloropyridazin-3-ones served as excellent novel N-acylating reagents for amines under neutral conditions in organic solvent. They are convenient, chemoselective and easy to handle stable N-acylating reagents of amines.

Key words

2-acylpyridazin-3-one - chemoselective N-acylation - pyridazinone

Full Text

References

1a Greene TW. Wuts PGM. Protective Groups in Organic Synthesis Wiley; New York: 1999. p.494-564

1b Mulzer J. In Comprehensive Organic Synthesis Vol. 6: Trost BM. Fleming I. Pergamon; Oxford: 1991. p.323-417

2 Vogel A. Practical Organic Chemistry Longman Scientific & Technical and Wiley; New York: 1989. p.708-710

3 Smith MB. March J. March’s Advanced Organic Chemistry 5th ed: Wiley; New York: 2001. p.506-512

4a Staab HA. Walther G. Angew. Chem. 1960, 72: 35

4b Itoh M. Hagiwara D. Kamiya T. Bull. Chem. Soc. Jpn. 1977, 50: 718

4c Kunieda T. Higuchi T. Abe Y. Hirobe M. Tetrahedron Lett. 1982, 23: 1159

4d Kita Y. Haruta J. Yasuda H. Fukunaga K. Shirouchi Y. Tamura Y. J. Org. Chem. 1982, 47: 2697

4e Husson A. Besselievre R. Husson H.-P. Tetrahedron Lett. 1983, 24: 1031

4f Joshua AV. Scott JR. Tetrahedron Lett. 1984, 25: 5725

4g Kunieda T. Higuchi T. Abe Y. Hirobe M. Chem. Pharm. Bull. 1984, 32: 2174

4h Nagao Y. Seno K. Kawabata K. Miyasaka T. Takao S. Fujita E. Chem. Pharm. Bull. 1984, 32: 2687

4i Atwell GJ. Denny WA. Synthesis 1984, 1032

4j Murahashi S.-I. Naota T. Saito E. J. Am. Chem. Soc. 1986, 108: 7846

4k Murahashi S.-I. Naota T. Nakajima N. Chem. Lett. 1987, 879

4l Sharma SK. Miller MJ. Payne SM. J. Med. Chem. 1989, 32: 357

4m Kikugawa Y. Mitsui K. Sakamoto T. Kawase M. Tamiya H. Tetrahedron Lett. 1990, 31: 243

4n Keumi T. Shimada M. Morita T. Kitajima H. Bull. Chem. Soc. Jpn. 1990, 63: 2252

4o Akikusa N. Mitsui K. Sakamoto T. Kikugawa Y. Synthesis 1992, 1058

4p Murahashi S.-I. Naota T. Synthesis 1993, 433

4q Katritzky AR. Chang HX. Synthesis 1995, 503

4r O’Sullivan MC. Dalrymple DM. Tetrahedron Lett. 1995, 36: 3451

4s Xu D. Prasad K. Repic O. Blacklock TJ. Tetrahedron Lett. 1995, 36: 7357

4t Atkinson RS. Barker E. Sutcliffe MJ. Chem. Commun. 1996, 1051

4u Katritzky AR. Yang B. Semenzin D. J. Org. Chem. 1997, 62: 726

4v Blagbrough IS. Geall AJ. Tetrahedron Lett. 1998, 39: 439

4w Yasuhara T. Nagaoka Y. Tomioka K. J. Chem. Soc., Perkin Trans. 1 1999, 2233

4x Kondo K. Sekimoto E. Nakao J. Murakami Y. Tetrahedron 2000, 56: 5843

4y Katritzky AR. He H.-Y. Suzuki K. J. Org. Chem. 2000, 65: 8210

4z Wakasugi K. Nakamura A. Tanabe Y. Tetrahedron Lett. 2001, 42: 7427

5a Choi SY. Lee SG. Yoon YJ. J. Heterocycl. Chem. 1991, 28: 1235

5b Choi SY. Shin SC. Yoon YJ. J. Heterocycl. Chem. 1991, 28: 385

5c Kang YJ. Chung H.-A. Kweon DH. Cho SD. Lee SG. Kim SK. Yoon YJ. J. Heterocycl. Chem. 1998, 35: 595

5d Kweon DH. Kang YJ. Chung H.-A. Yoon YJ. J. Heterocycl. Chem. 1998, 35: 819

6a Chung H.-A. Kang YJ. Chung JW. Cho SD. Yoon YJ. J. Heterocycl. Chem. 1999, 36: 277

6b Chung H.-A. Kang YJ. Chung JW. Kweon DH. Yoon YJ. J. Heterocycl. Chem. 1999, 36: 413

7 CRC Handbook of Chemistry and Physics 81st Ed.: Lide DR. CRC Press; Boca Raton: 2000.