STRUCTURE OF 2,3-DIHYDRO-1-METHYLQUINOLIN-2-SPIRO-2'-INDIAN-3'-SPIRO-2''-(1'',3''-DITHIANE)-4,1'-DIONE

被引:3
|
作者
BEDDOES, RL
GRIERA, R
ALVAREZ, M
JOULE, JA
机构
[1] UNIV MANCHESTER,DEPT CHEM,MANCHESTER M13 9PL,LANCS,ENGLAND
[2] UNIV BARCELONA,FAC PHARM,ORGAN CHEM LAB,E-08028 BARCELONA,SPAIN
关键词
D O I
10.1107/S0108270192002531
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
C21H19NO2S2, M(r) = 381.51, monoclinic, C2/c, a = 24.911 (4), b = 10.028 (2), c = 17.042 (2) angstrom, beta = 121.367 (8)-degrees, V = 3634.8 (9) angstrom3, Z = 8, D(x) = 1.394 g cm-3, lambda(Cu Kalpha) = 1.54178 angstrom, mu = 27.25 cm -1, F(000) = 1600, T = 295 K, R = 0.036 for 2385 observed [I/sigma(I) greater-than-or-equal-to 3] reflexions. The dithiane ring adopts a flattened chair conformation; in the dihydroquinolone ring both the N-methyl and the carbonyl group are essentially coplanar with the benzene ring; the spiro junction is made with the indanone carbonyl pseudo equatorial and the spirodithiane linked pseudo axially. The structure shows the novel result of attempted tandem addition (nucleophile then electrophile; at 2-C then 3-C positions in a quinolin-4-one) of methyl 2-formylbenzoate dithiane anion to 1-methylquinolin-4-one. A mechanistic explanation is suggested.
引用
收藏
页码:2154 / 2157
页数:4
相关论文
共 50 条
  • [21] Acenapthene-2-spiro-5′-perhydrodipyrrolo[1,2-a;-2′,1′-c]pyrazine-6′-spiro-2"-acenapthene-1,1"-dione
    Sugaleshini, S.
    Gayathri, D.
    Velmurugan, D.
    Ravikumar, K.
    Sureshbabu, A. R.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2006, 62 : O2432 - O2434
  • [22] 1′-Methylcyclooctane-1-spiro-3′-pyrrolidine-2′-spiro-3"-indoline-2,2"-dioneand1,1′-dimethylpiperidine-3-spiro-3′-pyrrolidine-2′-spiro-3"-indoline-2",4-dione
    Suresh, J.
    Kumar, R. Suresh
    Perumal, S.
    Natarajan, S.
    ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2007, 63 (o538-o542): : O538 - O542
  • [23] 1′,1"-Dimethyl-4′-(naphthalen-1-yl)-1,2,3,4-tetrahydronaphthalene-2-spiro-3′-pyrrolidine-2′-spiro-3"-indoline-1,2"-dione
    Selvanayagam, S.
    Ravikumar, K.
    Saravanan, P.
    Raghunathan, R.
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O751 - U1223
  • [24] 1,2,3,4-Tetrahydro-4′-furfuryl-1′-methylnaphthalene-2-spiro-3′-pyrrolidine-2′-spiro-1"-acenaphthene-1,2"-dione
    Govind, MM
    Selvanayagam, S
    Velmurugan, D
    Ravikumar, K
    Durga, RR
    Raghunathan, R
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2003, 59 : O1875 - O1877
  • [25] 4′-(4-methoxyphenyl)-1′-methyl-4",5",6",7"-tetrahydro-1H-indole-3-spiro-2′-pyrrolidine-3′-spiro-2"-(thiazolo[3,2-a]pyrimidine)-2(3H),-3"(2"H)-dione
    Li, XF
    Feng, YQ
    Shi, DX
    Chen, HL
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2003, 59 : O1418 - O1419
  • [26] 1′-methyl-4′-phenyl-1H-indole-3-spiro2′-pyrrolidine-3′-spiro-1"-cyclooctane-2(3H), 2"-dione
    Kumar, R. Ganesh
    Gayathri, D.
    Velmurugan, D.
    Ravikumar, K.
    Poornachandran, M.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2006, 62 : O4821 - O4823
  • [27] 4′-(2,4-Dichlorophenyl)-1,1′-dimethylpiperidine-3-spiro-3′-pyrrolidine-2′-spiro-3"-indoline-4,2"-dione
    Nagamuthu, S.
    Sribala, R.
    Ranjithkumar, R.
    Krishnakumar, R. V.
    Srinivasan, N.
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : O717 - U5877
  • [28] 4′-(4-chlorophenyl)-1′-methyl-4",5",6",7"-tetrahydro-1H-indole-3-spiro-2′-pyrrolidine-3′-spiro-2"-(thiazolo[3,2-a]pyrimidine)-2(3H),-3"(2"H)-dione
    Li, XF
    Feng, YQ
    Gao, B
    Li, N
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2003, 59 : O1624 - O1625
  • [29] SYNTHESIS OF SPIRO[2,3]HEXENES AND A SPIRO[2,3]HEXADIENE
    SEMMELHACK, MF
    DEFRANCO, RJ
    TETRAHEDRON LETTERS, 1971, (16) : 1061 - +
  • [30] Synthesis of 3′,4′-Dihydro-2H, 2′H,5H-spiro [imidazolidine-4,1′-naphthalene]-2,5-dione and its Derivatives
    Marinov, Marin
    Marinova, Petja
    Stoyanov, Neyko
    Markova, Nadezhda
    Enchev, Venelin
    ACTA CHIMICA SLOVENICA, 2014, 61 (02) : 420 - 424