POLYCYCLIC N-HETEROCYCLIC COMPOUNDS 74: REARRANGEMENT REACTION OF 5-AMINO-1,2-DIHYDROFURO[2,3-c]ISOQUINOLINES WITH α,ω-DIBROMOALKANES AND EVALUATION OF PRODUCT BRONCHODILATOR ACTIVITY

被引：1

作者：

Okuda, Kensuke ^{[1
]}

Yoshida, Masahiko ^{[2
]}

Hirota, Takashi ^{[2
]}

Sasaki, Kenji ^{[2
]}

机构：

[1] Gifu Pharmaceut Univ, Lab Med & Pharmaceut Chem, Gifu 5011196, Japan

[2] Okayama Univ, Fac Pharmaceut Sci, Okayama 700, Japan

来源：

SYNTHETIC COMMUNICATIONS | 2012年 / 42卷 / 06期

关键词：

Bronchodilator activity; furo[2,3-c]isoquinoline; rearrangement; ring cleavage; spiroheterocycle; CLEAVAGE;

D O I：

10.1080/00397911.2010.532899

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of 5-amino-1,2-dihydrofuro[2,3-c]isoquinolines with 1,2-dibromoethane and 1,3-dibromopropane in the presence of a base afforded 2',3'-dihydrospiro[cyclopropane-1,6'(5'H)-imidazo[2,1-a]isoquinolin]-5'-ones land 3',4'-dihydro-2'H-spiro[cyclopropane-1,7'(6'H)-pyrimido[2,1-a]isoquinolin]-6'-ones, respectively. Certain of the products showed significant bronchodilator activity.

引用

页码：865 / 871

页数：7

共 18 条

[1] Polycyclic N-Heterocyclic Compounds. Part 63 Improved Synthesis of 5-Amino-1,2-dihydrofuro[2,3-c]isoquinolines via Truce-Smiles Rearrangement and Subsequent Formation to Furo[2,3-c]isoquinoline
Okuda, Kensuke
Yoshida, Masahiko
Hirota, Takashi
Sasaki, Kenji
CHEMICAL & PHARMACEUTICAL BULLETIN, 2010, 58 (03) : 363 - 368
[2] Polycyclic N-Heterocyclic Compounds 73: Synthesis and Evaluation of 5-Substituted 1,2-Dihydrofuro[2,3-c]isoquinolines as Inducers of Lipoprotein Lipase mRNA Expression
Okuda, Kensuke
Yoshida, Masahiko
Hirota, Takashi
Sasaki, Kenji
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2013, 50 : E9 - E11
[3] Polycyclic N-Heterocyclic Compounds. Part 64: Synthesis of 5-Amino-1,2,6,7-tetrahydrobenzo[f]furo[2,3-c]isoquinolines and Related Compounds. Evaluation of Their Bronchodilator Activity and Effects on Lipoprotein Lipase mRNA Expression
Okuda, Kensuke
Deguchi, Hiroshi
Kashino, Setsuo
Hirota, Takashi
Sasaki, Kenji
CHEMICAL & PHARMACEUTICAL BULLETIN, 2010, 58 (05) : 685 - 689
[4] Polycyclic N-Heterocyclic Compounds, Part 71: Synthesis and Bronchodilator Evaluation of 5-Substituted 1,2-Dihydrofuro[3,2-f][1,7]naphthyridines and Related Compounds
Okuda, Kensuke
Matsushita, Tetsuo
Hirota, Takashi
Sasaki, Kenji
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2012, 49 (04) : 742 - 747
[5] POLYCYCLIC N-HETEROCYCLIC COMPOUNDS. PART 70: SYNTHESIS OF 5-AMINO-1,2-DIHYDROFURO[2,3-b]PYRIDO[3′,2′:4,5]-THIENO[3,2-d]PYRIDINES AND RELATED COMPOUNDS. EVALUATION OF EFFECTS ON LIPOPROTEIN LIPASE mRNA EXPRESSION
Okuda, Kensuke
Takechi, Hideyasu
Hirota, Takashi
Sasaki, Kenji
HETEROCYCLES, 2011, 83 (06) : 1315 - 1328
[6] Polycyclic N-Heterocyclic Compounds. Part 65: Ring Cleavage Reactions of Fused Furo[2,3-c]isoquinolines and Related Compounds with Various Nucleophiles
Okuda, Kensuke
Deguchi, Hiroshi
Hirota, Takashi
Sasaki, Kenji
CHEMICAL & PHARMACEUTICAL BULLETIN, 2010, 58 (05) : 755 - 757
[7] Polycyclic N-Heterocyclic Compounds, Part 69: Synthesis of 5-amino-1,2-dihydro[1]benzofuro[3,2-d]furo[2,3-b]pyridines and their transformations to related compounds
Okuda, Kensuke
Takano, Jun-ichi
Hirota, Takashi
Sasaki, Kenji
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2012, 49 (02) : 281 - 287
[8] ON TRIAZOLES .18. AN UNEXPECTED REARRANGEMENT OBSERVED DURING THE REACTION OF 5-AMINO-1,2,4-TRIAZOLES WITH N-HETEROCYCLIC BETA-OXO-ESTERS
REITER, J
RIVO, E
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1989, 26 (04) : 971 - 980
[9] Polycyclic N-heterocyclic compounds. Part 61: A novel Truce-Smiles type rearrangement reaction of 4-(2-cyanovinyloxy)butanenitriles to give cycloalkeno[1,2-d]furo[2,3-b]pyridines
Okuda, Kensuke
Watanabe, Norimasa
Hirota, Takashi
Sasaki, Kenji
TETRAHEDRON LETTERS, 2010, 51 (06) : 903 - 906
[10] POLYCYCLIC N-HETEROCYCLIC COMPOUNDS, PART 77: SYNTHESIS OF [1]BENZOTHIENO[3′,2′:2,3]OXEPINO[4,5-d]PYRIMIDINES AND EVALUATION OF THEIR ANTIPLATELET AGGREGATION ACTIVITY
Okuda, Kensuke
Nikaido, Takashi
Hirota, Takashi
Sasaki, Kenji
SYNTHETIC COMMUNICATIONS, 2013, 43 (12) : 1619 - 1625

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