The application of disubstituted vinylogous iminium salts and related synthons to the regiocontrolled preparation of unsymmetrical 2,3,4-trisubstituted pyrroles

被引：57

作者：

Gupton, JT ^{[1
]}

Krumpe, KE

Burnham, BS

Dwornik, KA

Petrich, SA

Du, KX

Bruce, MA

Vu, P

Vargas, M

Keertikar, KM

Hosein, KN

Jones, CR

Sikorski, JA

机构：

[1] Univ N Carolina, Dept Chem, Asheville, NC 28804 USA

[2] Univ Cent Florida, Dept Chem, Orlando, FL 32816 USA

[3] GD Searle & Co, R&D, St Louis, MO 63198 USA

来源：

TETRAHEDRON | 1998年 / 54卷 / 20期

基金：

美国国家科学基金会;

关键词：

pyrroles; vinylogous iminium salts; vinylogous amides; chloroenals;

D O I：

10.1016/S0040-4020(98)00247-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reactions of 2,3-disubstituted chloropropeniminium salts and related synthons with ethyl glycinate, ethyl N-methylglycinate, and ethyl N-benzylglycinate have been studied tinder acidic, basic and neutral conditions. Such reactions have resulted in efficient and selective methodology for the synthesis of unsymmetrical 2,3,4-trisubstituted pyrrole systems. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：5075 / 5088

页数：14

共 11 条

[1] Convergent syntheses of the pyrrolic marine natural products lamellarin-O, lamellarin-Q, lukianol-A and some more highly oxygenated congeners
Banwell, MG
Flynn, BL
Hamel, E
Hockless, DCR
[J]. CHEMICAL COMMUNICATIONS, 1997, (02) : 207 - 208
[2] SYNTHESIS OF A NOVEL PYRROLO[2,3-D]PYRIMIDINE ALKALOID, RIGIDIN
EDSTROM, ED
WEI, Y
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (02) : 403 - 407
[3] FURSTNER A, 1995, J ORG CHEM, V60, P6637
[4] AN EFFICIENT, REGIOCONTROLLED SYNTHESIS OF 5-ARYL-2-CARBETHOXYPYRROLES FROM 3-ARYL-3-CHLOROPROPENIMINIUM SALTS
GUPTON, JT
KROLIKOWSKI, DA
YU, RH
VU, P
SIKORSKI, JA
DAHL, ML
JONES, CR
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (20) : 5480 - 5483
[5] The application of vinylogous iminium salts and related synthons to the regiocontrolled preparation of 2,3- and 2,5-disubstituted pyrroles
Gupton, JT
Petrich, SA
Smith, LL
Bruce, MA
Vu, P
Du, KX
Dueno, EE
Jones, CR
Sikorski, JA
[J]. TETRAHEDRON, 1996, 52 (20) : 6879 - 6892
[6] APPLICATION OF 2-SUBSTITUTED VINAMIDINIUM SALTS TO THE SYNTHESIS OF 2,4-DISUBSTITUTED PYRROLES
GUPTON, JT
KROLIKOWSKI, DA
YU, RH
RIESINGER, SW
SIKORSKI, JA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (15) : 4735 - 4740
[7] LIEBSCHER J, 1979, SYNTHESIS-STUTTGART, P241
[8] SYNTHESIS OF OCTAALKYLPORPHYRINS AND OCTAARYLPORPHYRINS FROM NITROALKENES
ONO, N
MARUYAMA, K
[J]. CHEMISTRY LETTERS, 1988, (09) : 1511 - 1514
[9] POLYCITONE A AND POLYCITRIN-A AND POLYCITRIN-B - NEW ALKALOIDS FROM THE MARINE ASCIDIAN POLYCITOR SP
RUDI, A
GOLDBERG, I
STEIN, Z
FROLOW, F
BENAYAHU, Y
SCHLEYER, M
KASHMAN, Y
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (05) : 999 - 1003
[10] TOTAL SYNTHESIS OF A MARINE ALKALOID, RIGIDIN
SAKAMOTO, T
KONDO, Y
SATO, S
YAMANAKA, H
[J]. TETRAHEDRON LETTERS, 1994, 35 (18) : 2919 - 2920

← 1 2 →