Unusual reactions of 5,5-dimethyl-2-(indenyl-2)-3-pyrazolidinone with acetylenedicarboxylates

被引：13
作者：
Turk, C [1 ]
Svete, J [1 ]
Stanovnik, B [1 ]
Golic, L [1 ]
Golobic, A [1 ]
Selic, L [1 ]
机构：
[1] Univ Ljubljana, Fac Chem & Chem Technol, Ljubljana 1000, Slovenia
来源：
ORGANIC LETTERS | 2000年 / 2卷 / 04期
关键词：
D O I：
10.1021/ol9911829
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[GRAPHICS] Reaction of 5,5-dimethyl-3-pyrazolidinone (1) with 2-indanone (2) gave 5,5-dimethyl-2-(1H-indenyl-2)-3-pyrazolidinone (3) instead of the expected azomethine imine 4. Although reaction of 2 substituted 3-pyrazolidinones with acetylenedicarboxylates usually gives ring expansion products, such as 1,2-diazepines, treatment of 3 with dialkyl acetylenedicarboxylates (5, R = Me; 6 R = Et) resulted in the formation of rel-(7aR,12aS)-6,7-bis (alkoxycarbonyl)-3,4-dihydro-4,4-dimethyl-7aH-indano[1,2-b]pyrrolo[1,2-a]pyrimidin-2-ones (7, R = Me; 9, R = Et) as major products and 3,4-bis(alkoxycarbonyl)-7,7-dimethyl-2-(indenyl-2)-6,7-dihydro-2H,6H-1,2-diazepin-5-ones (8, R = Me: 10, R = Et) as minor products.
引用
收藏
页码：423 / 424
页数：2
相关论文
共 50 条
  • [41] THE STEREOCHEMISTRY OF THE PHOSPHORUS-SELENIUM BOND .7. STRUCTURE OF 5,5-DIMETHYL-2-(ORTHO-NITROPHENYL)AMINO-1,3,2-DIOXAPHOSPHORINANE 2-SELENIDE
    WOLF, WM
    BARTCZAK, TJ
    [J]. ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1989, 45 : 1767 - 1770
  • [42] SOME REACTIONS OF 3-AMINO-5,5-DIMETHYL-2-PHENYL-1,2,4- OXADIAZOLINE
    HULL, R
    FARRAND, R
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1963, (DEC): : 6028 - &
  • [43] [3+2]-cycloaddition reactions of 2-phenyliodonio-5,5-dimethyl-1,3-dioxacyclohexanemethylide
    Gogonas, EP
    Hadjiarapoglou, LP
    [J]. TETRAHEDRON LETTERS, 2000, 41 (48) : 9299 - 9303
  • [44] Synthesis and Solubility of 5,5-Dimethyl-2-(phenyl(phenylamino)methyl)-1,3,2-dioxaphosphinane 2-oxide in Selected Solvents between 278.15 K and 347.15 K
    Ma, Xiao
    Zhao, Qianqiong
    Liu, Qianwen
    Xing, Yalin
    Fan, Ruilan
    Tian, Rongkai
    [J]. JOURNAL OF CHEMICAL AND ENGINEERING DATA, 2017, 62 (12) : 4196 - 4204
  • [45] Crystal structure of (2S,4S)-5,5-dimethyl-2-(pyridin-2-yl)-1,3-thiazolidine-4-carboxylic acid
    Laskar, Payel
    Kuwamura, Naoto
    Yoshinari, Nobuto
    Konno, Takumi
    [J]. ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2014, 70 : O1264 - +
  • [46] 5,5-Dimethyl-3-(5-methylisoxazol-3-yl)cyclohex-2-enone
    Scott, KR
    Butcher, RJ
    Hanson, CD
    [J]. ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2006, 62 : O218 - O220
  • [47] UNUSUAL S-METHYLATION OF 5,5-DIMETHYL-2-PHENYLSULFENYL-1,3-CYCLOHEXANEDIONE WITH DIAZOMETHANE
    ARBUZOV, BA
    BELKIN, YV
    POLEZHAEVA, NA
    [J]. BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1976, 25 (10): : 2251 - 2252
  • [48] Femtosecond proton transfer studies of 5,5′-dimethyl-[2,2′-bipyridyl]-3,3′-diol
    Marks, D
    Zhang, H
    Glasbeek, M
    [J]. JOURNAL OF LUMINESCENCE, 1998, 76-7 : 52 - 55
  • [49] Femtosecond proton transfer studies of 5,5′-dimethyl-[2,2′-bipyridyl]-3,3′-diol
    Marks, D.
    Zhang, H.
    Glasbeek, M.
    [J]. Journal of Luminescence, 1998, 76-77 : 52 - 55
  • [50] 5,5′-Dimethyl-2,2′-dithiodi-1,3,4-thiadiazole
    Song, JL
    Zhou, WB
    Zeng, HY
    Dong, ZC
    [J]. ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2002, 58 : O1045 - O1047
12345