Synthesis and Stereochemistry of 3,7-Diazatricyclo[4.2.2.2^<2,5>]dodeca-9,11-dienes Derived by [4+4] Cyclodimerization of 2,3-Dihydroisoquinoline Derivatives

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概要

• 論文の詳細を見る

• 2-Acyl(or sulfonyl)-c-4-bromo-γ-1-cyano-t-3-methoxy-1,2,3,4-tetrahydroisoquinolines 2b-g when treated with triethylamine or K_2CO_3 gave cyclodimers 5b-g of 2-acyl(or sulfonyl)-1-cyano-3-methoxy-2,3-dihydroisoquinolines in high yields. The dimers are composed of two tetrahydroisoquinoline units fused at the 1,1'- and 4,4'-positions to form a triheterocyclic 3,7-diazatricyclo[4.2.2.2^<2,5>]dodeca-9,11-diene ring. 2,3-Dihydroisoquinoline type compounds 3 are the key intermediate for this unusual [4+4] cyclodimerization. The structures of the dimers with an exo-type configuration have been determined by X-ray crystallography. The reaction mechanism of the cyclodimerization is discussed in conjunction with the stereochemistry of the products.

• 公益社団法人日本薬学会の論文
• 1998-12-15

著者

• HATANO Keiichiro

  Faculty of Pharmaceutical Sciences, Nagoya City University

• Hirota M

  Department Of Synthetic Chemistry Faculty Of Engineering Yokohama National University

• HATANO Keiichiro

  Graduate School of Pharmaceutical Sciences, Nagoya City University

• Sugiura M

  Research Division The Green Cross Corporation

• Hamada Y

  Faculty Of Pharmacy Meijo University

• Kurono Y

  Department Of Pharmaceutics Faculty Of Pharmaceutical Engineering Nagoya City University

• Kurono Yukihisa

  Faculty Of Pharmaceutical Sciences Nagoya City University

• Suezawa H

  Ministry Of Education Culture Sports Science And Technology

• Hatano K

  Graduate School Of Pharmaceutical Sciences Nagoya City University

• Hatano Keiichiro

  Faculty Of Pharmaceutical Sciences Nagoya City University

• SUEZAWA Hiroko

  Instrumental Analysis Center, Yokohama National University

• SUGIURA Michiharu

  Faculty of Pharmacy, Meijo University

• ASAI Koosuke

  Faculty of Pharmacy, Meijo University

• HAMADA Yoshiki

  Faculty of Pharmacy, Meijo University

• HIROTA Minoru

  Instrumental Analytical Center, Yokohama National University

• Suezawa Hiroko

  Instrumental Analysis Center Yokohama National University

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