Intramolecular cyclization reactions of aziridines with π-nucleophiles

被引:30
|
作者
Bergmeier, SC [1 ]
Katz, SJ [1 ]
Huang, JF [1 ]
McPherson, H [1 ]
Donoghue, PJ [1 ]
Reed, DD [1 ]
机构
[1] Ohio Univ, Dept Chem & Biochem, Athens, OH 45701 USA
基金
美国国家科学基金会;
关键词
aziridines; amines; bicyclic heterocyclic compounds;
D O I
10.1016/j.tetlet.2004.05.009
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We have found that aziridines will react with a variety of pi-nucleophiles in intramolecular cyclization reactions to produce nitrogen containing core structures found in a variety of bioactive molecules. These cyclizations are more general and facile than corresponding intermolecular reactions. We have examined the effects of ring size, pi-nucleophile identity and substitution on this reaction. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5011 / 5014
页数:4
相关论文
共 50 条
  • [31] INTRAMOLECULAR CYCLIZATION REACTIONS IN ALIPHATIC THYMIDINE ANALOGS SERIES
    SKARIC, V
    RAZA, Z
    SKARIC, D
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (01): : 223 - 227
  • [32] REACTIONS OF SULFUR YLIDES - NEW EXAMPLE OF INTRAMOLECULAR CYCLIZATION
    LOZINSKII, MO
    KUKOTA, SN
    BODNAR, VN
    PELKIS, PS
    ZHURNAL ORGANICHESKOI KHIMII, 1973, 9 (01): : 216 - 217
  • [33] CYCLIZATION REACTIONS OF N-PERFLUOROVINYLIMINOCARBOXYLIC ACID-CHLORIDES WITH NUCLEOPHILES
    DRACH, BS
    KOVALEV, VA
    KIRSANOV, AV
    ZHURNAL ORGANICHESKOI KHIMII, 1976, 12 (03): : 673 - 678
  • [34] CYCLIZATION REACTIONS OF CHLOROSUBSTITUTED 2-AZONIAALLENE SALTS WITH BIFUNCTIONAL NUCLEOPHILES
    HAMED, A
    SYNTHESIS-STUTTGART, 1992, (06): : 591 - 595
  • [35] Addition-cyclization reactions of cinnamoyl isothiocyanate with nitrogen and oxygen nucleophiles
    Ahmed, AFS
    Aouf, N
    Assy, MG
    JOURNAL OF CHEMICAL RESEARCH, 1998, (09) : 508 - 509
  • [36] CYCLIZATION OF AZIDOFORMATES, FORMATION OF AZIRIDINES
    RHOUATI, S
    BERNOU, A
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (11) : 730 - 732
  • [37] SYNTHESIS OF SUBSTITUTED AZIRIDINES VIA INTRAMOLECULAR REACTIONS OF β-N-CHLOROETHYLAMINO CARBANIONS
    Makosza, Mieczyslaw
    Bobryk, Karolina
    Krajewski, Dariusz
    HETEROCYCLES, 2008, 76 (02) : 1511 - 1524
  • [38] REACTIONS OF CARBAMYLIMIDAZOLES WITH NUCLEOPHILES - EXAMPLE OF AN INTRAMOLECULAR ACYL TRANSFER-REACTION
    EHLER, KW
    JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (18): : 3041 - 3042
  • [39] An Organocatalytic Kinetic Resolution of Aziridines by Thiol Nucleophiles
    Sun, Song
    Wang, Zhaobin
    Li, Shijia
    Zhou, Cong
    Song, Lijuan
    Huang, Hai
    Sun, Jianwei
    ORGANIC LETTERS, 2021, 23 (02) : 554 - 558
  • [40] INTRAMOLECULAR REACTIONS .5. FACTORS AFFECTING THE YIELD IN DIAZONIUM CYCLIZATION REACTIONS
    DETAR, DLF
    WHITELEY, TE
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (10) : 2498 - 2502