Access to pyrralo- and pyrido[1,2-a]indole derivatives by intramolecular nitrone cycloadditions.: Effect of steric factors on the regioselective product formation

被引:38
作者
Beccalli, EM
Broggini, G
La Rosa, C
Passarella, D
Pilati, T
Terraneo, A
Zecchi, G
机构
[1] Univ Milan, Fac Farm, Ist Chim Organ, I-20133 Milan, Italy
[2] Univ Insubria, Dipartimento Sci Chim Fis & Matemat, I-22100 Como, Italy
[3] Univ Milan, Dipartimento Chim Organ & Ind, I-20133 Milan, Italy
[4] CNR, Ctr Relaz Struttura & Reatt Chim, I-20133 Milan, Italy
关键词
D O I
10.1021/jo000842g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
On starting from N-allyl-substituted 2-indolecarbaldehydes and exploiting the intramolecular nitrone cycloaddition methodology, we synthesized a number of the title fused-ring indole derivatives in racemic as well as enantiopure form.
引用
收藏
页码:8924 / 8932
页数:9
相关论文
共 25 条
[1]   ELECTROSTATIC EFFECTS IN 1,3-DIPOLAR CYCLOADDITION REACTIONS TO CHIRAL ALLYL ETHERS - A RATIONALE FOR THE EXPERIMENTALLY OBSERVED DIASTEREOSELECTIVITIES [J].
ANNUNZIATA, R ;
BENAGLIA, M ;
CINQUINI, M ;
RAIMONDI, L .
TETRAHEDRON, 1993, 49 (38) :8629-8636
[2]   Intramolecular cycloadditions of nitrones derived from 1-allyl-2-pyrrolecarbaldehyde as a route to racemic and enantiopure pyrrolizidines and indolizidines [J].
Arnone, A ;
Broggini, G ;
Passarella, D ;
Terraneo, A ;
Zecchi, G .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (25) :9279-9284
[3]   A new synthesis of furostifoline [J].
Beccalli, EM ;
Clerici, F ;
Marchesini, A .
TETRAHEDRON, 1998, 54 (38) :11675-11682
[4]  
Beccalli EM, 1999, EUR J ORG CHEM, V1999, P1421, DOI 10.1002/(SICI)1099-0690(199906)1999:6<1421::AID-EJOC1421>3.0.CO
[5]  
2-O
[6]   A new synthesis of staurosporinone [J].
Beccalli, EM ;
Gelmi, ML ;
Marchesini, A .
TETRAHEDRON, 1998, 54 (24) :6909-6918
[7]   SYNTHESIS OF DIHYDROISOXAZOLO AND TETRAHYDROISOXAZOLO[3',4'-3,4]PYRROLO[1,2-A]INDOLES VIA INTRAMOLECULAR CYCLO-ADDITIONS - A NOVEL CLASS OF MITOMYCIN ANALOGS [J].
BHUYAN, PJ ;
BORUAH, RC ;
SANDHU, JS .
TETRAHEDRON LETTERS, 1989, 30 (11) :1421-1422
[8]   NITRONES AND OXAZIRIDINES .45. FORMATION OF PYRROLO[1,2-A]INDOLES BY INTRAMOLECULAR NITRONE CYCLOADDITION [J].
BLACK, DS ;
CRAIG, DC ;
DEBDAS, RB ;
KUMAR, N .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1993, 46 (05) :603-622
[9]   Synthesis of enantiopure 3-hydroxymethylchromanes via intramolecular nitrone cycloaddition [J].
Broggini, G ;
Folcio, F ;
Sardone, N ;
Sonzogni, M ;
Zecchi, G .
TETRAHEDRON-ASYMMETRY, 1996, 7 (03) :797-806
[10]  
Franck R. W., 1986, PROGR CHEM ORGANIC N, V50, P27