A concise access to 6-azabicyclo[3.1.0] hexanes via high-pressure promoted cycloaddition reaction of azides to ABH

被引：13

作者：

Ishikura, M ^{[1
]}

Kudo, S ^{[1
]}

Hino, A ^{[1
]}

Ohnuki, N ^{[1
]}

Katagiri, N ^{[1
]}

机构：

[1] Hlth Sci Univ Hokkaido, Fac Pharmaceut Sci, Ishikari, Hokkaido 0610293, Japan

来源：

HETEROCYCLES | 2000年 / 53卷 / 07期

关键词：

azamethano-carbocyclic nucleoside; anti-HIV; aziridine; bicycloamide; high-pressure reaction;

D O I：

10.3987/COM-00-8902

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cycloaddition reaction of electron-deficient azides (5a, b) to 2-azabicyclo[2.2.1]hept-5-en-3-one (ABH) (1) was accelerated by high-pressure, leading to a mixture of regioisomeric triazolines (6) in good yields. Then, 6 were in turn, through photolysis and ring opening sequences, converted to 6-azabicyclo[3.1.0]-hexanes (8).

引用

页码：1499 / 1504

页数：6

共 16 条

[1] 1',6'-METHANO CARBOCYCLIC THYMIDINE - SYNTHESIS, X-RAY CRYSTAL-STRUCTURE, AND EFFECT ON NUCLEIC-ACID DUPLEX STABILITY [J].

ALTMANN, KH ;

IMWINKELRIED, R ;

KESSELRING, R ;

RIHS, G .

TETRAHEDRON LETTERS, 1994, 35 (41) :7625-7628

[2] 4',6'-METHANO CARBOCYCLIC THYMIDINE - A CONFORMATIONALLY CONSTRAINED BUILDING-BLOCK FOR OLIGONUCLEOTIDES [J].

ALTMANN, KH ;

KESSELRING, R ;

FRANCOTTE, E ;

RIHS, G .

TETRAHEDRON LETTERS, 1994, 35 (15) :2331-2334

[3] HIGH-PRESSURE INDUCED 1,3-DIPOLAR CYCLOADDITIONS OF AZIDES WITH ELECTRON-DEFICIENT OLEFINS [J].

ANDERSON, GT ;

HENRY, JR ;

WEINREB, SM .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (24) :6946-6948

[4] SYNTHESIS OF (1R,3R,5S)-1-AMINO-3-(HYDROXYMETHYL)BICYCLO[3.1.0]HEXANE AS A PRECURSOR FOR THE SYNTHESIS OF CARBOCYCLIC NUCLEOSIDES [J].

CHANG, HS ;

BERGMEIER, SC ;

FRICK, JA ;

BATHE, A ;

RAPOPORT, H .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (18) :5336-5342

[5] Enantiomeric syntheses of conformationally restricted D- and L-2′,3′-dideoxy-2′,3′-endo-methylene nucleosides from carbohydrate chiral templates [J].

Chun, BK ;

Olgen, S ;

Hong, JH ;

Newton, MG ;

Chu, CK .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (03) :685-693

[6] ORGANIC-REACTIONS AT HIGH-PRESSURE - DIPOLAR CYCLOADDITION RING CONTRACTION REACTIONS OF HINDERED SILYL ENOL ETHERS AND ARYLSULFONYL AZIDES [J].

DAUBEN, WG ;

BUNCE, RA .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (25) :5042-5044

[7] ULTRASONICALLY ACCELERATED CYCLOADDITION - REARRANGEMENT OF ENOL ETHERS [J].

GOLDSMITH, D ;

SORIA, JJ .

TETRAHEDRON LETTERS, 1991, 32 (22) :2457-2460

[8] Synthesis of novel D-2′,3′-dideoxy-2′,3′-endo-methylene nucleosides [J].

Hong, JH ;

Chun, BK ;

Chu, CK .

TETRAHEDRON LETTERS, 1998, 39 (3-4) :225-228

[9] 1.3-DIPOLARE CYCLOADDITIONEN .22. ZUR ANLAGERUNG ORGANISCHER AZIDE AN WINKELGESPANNTE DOPPELBINDUNGEN [J].

HUISGEN, R ;

MOBIUS, L ;

MULLER, G ;

STANGL, H ;

SZEIMIES, G ;

VERNON, JM .

CHEMISCHE BERICHTE-RECUEIL, 1965, 98 (12) :3992-&

[10] The first synthesis of a 2′,3′-methane carbocyclic nucleoside [J].

Katagiri, N ;

Yamatoya, Y ;

Ishikura, M .

TETRAHEDRON LETTERS, 1999, 40 (51) :9069-9072

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