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J-GLOBAL ID：200902228225328121   Reference number：07A0060781

REACTION OF FUNCTIONALIZED AZOMETHINE YLIDES WITH OLEFINIC DIPOLAROPHILES

官能化アゾメチンイリドとオレフィン系親双極子試薬との反応

Author (3)： KAWASHIMA Keisuke (Yamaguchi Univ., Ube, JPN) ,  KAHEHI Akikazu (Shinshu Univ., Nagano, JPN) ,  NOGUCHI Michihiko (Yamaguchi Univ., Ube, JPN)
Material： Heterocycles  (International Journal for Reviews and Communications in Heterocyclic Chemistry)
Volume： 70  Page： 647-654  Publication year： Dec. 31, 2006 
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： lactam ,...

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JST classification (4)： Pyrimidines  (CF07103W) ,  Aliphatic carboxylic esters,anhydrides,acid halides,acyl peroxides  (CF03210P) ,  Pyrroles  (CF07076L) ,  Cyclization reaction,ring-opening reaction  (CF02050I)

Substance index (21)： Pyridinium・p-toluenesulfonate ,  Acrylic acid methyl ,  Crotonic acid methyl ,  L-Phenylalanine methyl ,  Fumaric acid dimethyl ,  Maleic acid dimethyl ,  Methacrylic acid methyl ,  2-(Dimethylamino)-3-formyl-4H-pyrido[1,2-a]pyrimidine-4-one ,  (E)-1-Oxo-1-methoxy-2-benzyl-4-[2-(dimethylamino)-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-yl]-3-azonia-3-butene-2-ide ,  2-Benzyl-5β-[2-(dimethylamino)-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-yl]pyrrolidine-2β,4α-dicarboxylic acid dimethyl ester ,  4-Methyl-2-benzyl-5β-[2-(dimethylamino)-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-yl]pyrrolidine-2β,4α-dicarboxylic acid dimethyl ester ,  3β-Methyl-2-benzyl-5β-[2-(dimethylamino)-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-yl]pyrrolidine-2β,4α-dicarboxylic acid dimethyl ester ,  2-Benzyl-5β-[2-(dimethylamino)-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-yl]pyrrolidine-2β,3β,4α-tricarboxylic acid trimethyl ester ,  4-Methyl-2-benzyl-5β-[2-(dimethylamino)-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-yl]pyrrolidine-2β,4β-dicarboxylic acid dimethyl ester ,  3α-Methyl-2-benzyl-5β-[2-(dimethylamino)-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-yl]pyrrolidine-2β,4β-dicarboxylic acid dimethyl ester ,  2-Benzyl-5β-[2-(dimethylamino)-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-yl]pyrrolidine-2β,3β,4β-tricarboxylic acid trimethyl ester ,  3β-Phenyl-2-benzyl-5β-[2-(dimethylamino)-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-yl]pyrrolidine-2β,4,4-tricarboxylic acid trimethyl ester ,  2-Benzyl-4-methyl-3,4-dihydro-2H-pyrrole-2α,4α-dicarboxylic acid dimethyl ester ,  2-Benzyl-3β-methyl-2,3-dihydro-1H-pyrrole-2α,4-dicarboxylic acid dimethyl ester ,  2-Benzyl-2,3-dihydro-1H-pyrrole-2β,3β,4-tricarboxylic acid trimethyl ester ,  2-Benzyl-2,3-dihydro-1H-pyrrole-2α,3β,4-tricarboxylic acid trimethyl ester

Reference (7)：

• U. Obst, P. Betschmann, C. Lemer, P. Seiler, and F. Diederich Hely. Chim. Acta, 2000, 83, 855.(b) W. H. Pearson, In Studies in Natural Products Chemistry; ed. by Atta-Ur-Rahman; Elsevier: New York, 1998; Vol.1, 323-358.(c) G. W. Gribble, In Comprehensive Heterocyclic Chemistry; ed. by A. R. Katritzky, C. W. Rees and E. F. V. Scriven; Pergamon: Oxford, U. K., 1996; Vol.2, 207-257.
• M. Shirai, H. Kuwabara, S. Matsumoto, H. Yamamoto, A. Kakehi, and M. Noguchi Tetrahedron, 2003, 59, 4113.
• M. Noguchi, S. Matsumoto, M. Shirai, and H. Yamamoto Tetrahedron, 2003, 59, 4123.
• K. Kawashima, A. Kakehi, and M. Noguchi submitted to Tetrahedron.
• The structures of cycloadducts (5, 6 and 7) were characterized by their spectroscopic data. Moreover, the structures of five key cycloadducts (5b, 7b, 5c, 6d and 6e) were confirmed by single crystal X-Ray analysis and crystallographic data have been deposited with Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 622532 for 5b, CCDC 622531 for 7b, CCDC 622529 for 5c, CCDC 622530 for 6d and CCDC 622533 for 6e. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 IEZ, UK (fax:+ 44-1223-336033 or e-mail: [e-mail]).

Terms in the title (6)： 官能化 ,  アゾメチンイリド ,  オレフィン ,  親 ,  双極子 ,  試薬