Art

J-GLOBAL ID：201102277181668816   Reference number：11A0582400

HEXAMETHYLDISILAZANE-PROMOTED SONOGASHIRA REACTION OF POLYFUNCTIONALIZED N-CONTAINING HETEROCYCLES

多官能化N-含有複素環類のヘキサメチルジシラザン促進Sonogashira反応

Author (6)： INOUYE Masahiko (Univ. Toyama, Toyama, JPN) ,  DOI Yasuhiro (Univ. Toyama, Toyama, JPN) ,  AZUCHI Junichi (Univ. Toyama, Toyama, JPN) ,  SHIRATO Wataru (Univ. Toyama, Toyama, JPN) ,  CHIBA Junya (Univ. Toyama, Toyama, JPN) ,  ABE Hajime (Univ. Toyama, Toyama, JPN)
Material： Heterocycles  (International Journal for Reviews and Communications in Heterocyclic Chemistry)
Volume： 82  Issue： 2  Page： 1137-1141  Publication year： Mar. 01, 2011 
JST Material Number： S0966A  ISSN： 0385-5414  CODEN： HTCYAM  Document type： Article
Article type： 短報  Country of issue： Japan (JPN)  Language： ENGLISH (EN)

Thesaurus term： nitrogen heterocyclic compound ,  chemical synthesis ,  Sonogashira reaction ,  solvent effect ,  *C-nucleoside ,  Pyridines ,  Pyrimidines
Semi thesaurus term： Pyridines ,  Pyrimidines

JST classification (1)： Nucleosides,nucleotides  (CF10060K)

Substance index (7)： Hexamethyldisilazane ,  5-[[5-O-[Bis(4-methoxyphenyl)(phenyl)methyl]-2-deoxy-β-D-ribofuranosyl]ethynyl]-6-[[(dimethylamino)methylene]amino]pyridine-2(1H)-one ,  5-[[5-O-[Bis(4-methoxyphenyl)(phenyl)methyl]-3-O-(trimethylsilyl)-2-deoxy-β-D-ribofuranosyl]ethynyl]-6-[[(dimethylamino)methylene]amino]pyridine-2(1H)-one ,  5-[[5-O-[Bis(4-methoxyphenyl)(phenyl)methyl]-2-deoxy-β-D-ribofuranosyl]ethynyl]-4-aminopyrimidine-2(3H)-one ,  2-Amino-5-[[5-O-[phenylbis(4-methoxyphenyl)methyl]-2-deoxy-β-D-ribofuranosyl]ethynyl]pyrimidine-4(3H)-one ,  6-[[5-O-[Bis(4-methoxyphenyl)(phenyl)methyl]-2-deoxy-β-D-ribofuranosyl]ethynyl]-2-aminopyrimidine-4(3H)-one ,  6-[[5-O-[Bis(4-methoxyphenyl)(phenyl)methyl]-2-deoxy-β-D-ribofuranosyl]ethynyl]-2-[(dimethylamino)methyleneamino]pyrimidine-4(3H)-one

Reference (8)：

• For reviews for Sonogashira reaction, see: K. Sonogashira,‘Metal-catalyzed Cross-coupling Reactions,’ ed. by F. Diederich and P. J, Stang, WILEY-VCH, Weinheim, 1998, pp. 203-229; R. Chinchilla and C. Najera, Chem. Rev., 2007, 107, 874.
• Y. Doi, J. Chiba, T. Morikawa, and M. Inouye, J. Am. Chem. Soc., 2008, 130, 8762.
• For recent synthetic examples of alkynyl C-nucleosides by Sonogashira reaction, see:(a) T. Bobula, M. Hocek, and M. Kotora, Tetrahedron, 2010, 66, 530;(b) M. F. A. Adamo and R. Pergoli, Org. Lett., 2007, 9, 4443;(c) D. Heinrich, T. Wagner, and U. Diederichsen, Org. Lett., 2007, 9, 5311. In ref. 3c, a two-step procedure (persilylation of 5-iodocytosine in HMDS and Sonogashira reaction in DIPEA/DMF) was reported.
• M. Takase, T. Morikawa, H. Abe, and M. Inouye, Org. Lett., 2003, 5, 625.
• K. Fujimoto, S. Aizawa, I. Oota, J. Chiba, and M. Inouye, Chem. Eur. J., 2010, 16, 2401; K. Fujimoto, S. Yamada, and M. Inouye Chem. Commun., 2009, 7164; J. Chiba, S. Takeshima, K. Mishima, H. Maeda, Y. Nanai, K. Mizuno, and M. Inouye, Chem. Eur. J., 2007, 13, 8124.

Terms in the title (5)： 多官能 ,  複素環 ,  ヘキサメチルジシラザン ,  促進 ,  Sonogashira反応