Studies on the reactivity of N-(3-thienyl)carbamates

被引:24
作者
Brugier, D [1 ]
Outurquin, F [1 ]
Paulmier, C [1 ]
机构
[1] Univ Rouen, IRCOF UFR Sci, Lab Synthese Thio & Selenoorgan, F-76821 Mt St Aignan, France
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2001年 / 01期
关键词
D O I
10.1039/b003580g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
tert-Butyl 2-allyl- and N-allyl-3-thienylcarbamates were used as substrates for the preparation of thieno[3,2-b]pyrroles 9 and 5,6-dihydrothieno[3,2-b]pyrroles 10. Pd-catalyzed cyclization of N-allyl-(2-bromo3-thienyl)carbamates 12 has allowed access to thienopyrroles 9. The radical route has led to the formation of a dihydrothienopyrrole 10 or a tetrahydrothienopyridine 19 according to the beta -substitution of the allyl substituent. The nucleophilic participation of the tert-butoxycarbonyl group occurred during the selenium or iodine-induced cyclization of tert-butyl 2-allyl-or-N-allyl-3-thienylcarbamates. The formation of the thienooxazepinone 25 and N-(3-thienyl)oxazolidinones 28 and 29 was observed.
引用
收藏
页码:37 / 43
页数:7
相关论文
共 41 条
  • [31] SOLVENT EFFECTS IN THERMAL (2 + 2) CYCLOADDITION REACTIONS - INTRAMOLECULAR CAPTURE OF 1,4-DIPOLAR INTERMEDIATES VS (2 + 2) CYCLOADDITION IN REACTIONS OF 3-(1-PYRROLIDINYL)THIOPHENES WITH ELECTRON-DEFICIENT ACETYLENES
    REINHOUDT, DN
    GEEVERS, J
    TROMPENAARS, WP
    HARKEMA, S
    VANHUMMEL, GJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (02) : 424 - 434
  • [32] SAXTON JE, 1994, CHEM HETEROCYCL C S4, V25
  • [33] RESEARCH IN HETEROCYCLIC SERIES .29. PREPARATION THIENOPYRROLES, SELENOLOPYRROLES, FUROPYRROLES AND PYRROLOPYRROLES
    SOTH, S
    FARNIER, M
    PAULMIER, C
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1978, 56 (10): : 1429 - 1434
  • [34] Southon IW., 1989, DICT ALKALOIDS
  • [35] Iodosobenzene diacetate and diphenyl diselenide: An electrophilic selenenylating agent of double bonds
    Tingoli, M
    Tiecco, M
    Testaferri, L
    Temperini, A
    [J]. SYNTHETIC COMMUNICATIONS, 1998, 28 (10) : 1769 - 1778
  • [36] WEEB RR, 1983, TETRAHEDRON LETT, V24, P1357
  • [37] PALLADIUM-CATALYZED SYNTHESIS OF HETEROCONDENSED PYRROLES
    WENSBO, D
    ERIKSSON, A
    JESCHKE, T
    ANNBY, U
    GRONOWITZ, S
    COHEN, LA
    [J]. TETRAHEDRON LETTERS, 1993, 34 (17) : 2823 - 2826
  • [38] Indole-3-pyruvic acid oxime ethers and thieno analogues by Heck cyclisation. Application to the synthesis of thia-tryptophans.
    Wensbo, D
    Gronowitz, S
    [J]. TETRAHEDRON, 1996, 52 (47) : 14975 - 14988
  • [39] INDOLE 3-ACETIC ACIDS AND HETERO ANALOGS BY ONE-POT SYNTHESIS INCLUDING HECK CYCLIZATION
    WENSBO, D
    ANNBY, U
    GRONOWITZ, S
    [J]. TETRAHEDRON, 1995, 51 (37) : 10323 - 10342
  • [40] Synthesis of 2-dienylindole, SB 242784, by a three-component palladium-catalyzed coupling reaction
    Yu, MS
    de Leon, LL
    McGuire, MA
    Botha, G
    [J]. TETRAHEDRON LETTERS, 1998, 39 (51) : 9347 - 9350