CYCLIC GUANIDINES .4. INTRAMOLECULAR NUCLEOPHILIC AROMATIC-SUBSTITUTION OF HYDROGEN IN (3-NITROPHENYL)GUANIDINES

被引：0

作者：

ESSER, F ^{[1
]}

POOK, KH ^{[1
]}

机构：

[1] BOEHRINGER INGELHEIM KG,DEPT ANALYT CHEM,W-6507 INGELHEIM,GERMANY

来源：

SYNTHESIS-STUTTGART | 1992年 / 06期

关键词：

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclization of substituted (3-nitrophenyl)guanidines is achieved in basic medium by nucleophilic displacement of hydrogen. The reaction offers a new route to benzimidazoles as well as to tricyclic imidazo-, pyrimido- and diazepino-benzimidazoles with uncommon substitution patterns. The mechanism of the redox process is investigated and the regioselectivity is discussed in terms of substrate structure and reaction conditions. An outline is given on the scope of the ring closure.

引用

页码：596 / 601

页数：6

共 50 条

[31] EVIDENCE FOR NUCLEOPHILIC CATALYSIS IN THE AROMATIC-SUBSTITUTION REACTION CATALYZED BY (4-CHLOROBENZOYL)COENZYME-A DEHALOGENASE
YANG, G
LIANG, PH
DUNAWAYMARIANO, D
[J]. BIOCHEMISTRY, 1994, 33 (28) : 8527 - 8531
[32] NUCLEOPHILIC AROMATIC-SUBSTITUTION - TRANSMISSION OF SUBSTITUENT EFFECTS IN ALKALINE-HYDROLYSIS OF 4-AMINOPHENYLAZOBENZOTHIAZOLIUM DYES
DROZARIO, AP
WILLIAMS, A
PARTON, B
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1987, (12): : 1781 - 1784
[33] NUCLEOPHILIC AROMATIC SUBSTITUTION .4. STERIC EFFECTS IN THIOALCOXYDEHALOGENATION OF SOME HALOGENO-AROMATIC COMPOUNDS
BARTOLI, G
DINUNNO, L
TODESCO, PE
[J]. TETRAHEDRON LETTERS, 1968, (19) : 2369 - &
[34] Mechanism of intramolecular nucleophilic substitution in the catalytic hydrolysis of bis(4-nitrophenyl) phosphate ester in a metallomicelle
Jun, Li
Sang Xue-mei
Min, Wan
Chen Guo-xu
Xie Jia-qing
[J]. PROGRESS IN REACTION KINETICS AND MECHANISM, 2006, 31 (04) : 189 - 204
[35] STUDIES ON THE SYNTHESES OF HETEROCYCLIC-COMPOUNDS .865. A NOVEL SYNTHESIS OF INDOLE-DERIVATIVES BY INTRAMOLECULAR NUCLEOPHILIC AROMATIC-SUBSTITUTION
KAMETANI, T
OHSAWA, T
IHARA, M
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (01): : 290 - 294
[36] AROMATIC NUCLEOPHILIC SUBSTITUTION .4. REACTION OF PENTACHLORO DERIVATIVES OF BENZENE WITH SODIUM METHOXIDE
YAKOBSON, GG
KOBRINA, LS
VOROZHTS.NN
[J]. JOURNAL OF GENERAL CHEMISTRY USSR, 1965, 35 (01): : 136 - &
[37] SYNTHESIS OF 2,3-DIHYDRO-1H-PYRROLO[1,2-A]INDOLES BY INTRAMOLECULAR NUCLEOPHILIC AROMATIC-SUBSTITUTION
KAMETANI, T
TAKAHASHI, K
IHARA, M
FUKUMOTO, K
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (04): : 389 - 393
[38] REGIOSELECTIVITY IN INTRAMOLECULAR NUCLEOPHILIC AROMATIC-SUBSTITUTION - SYNTHESIS OF THE POTENT ANTI HIV-1 8-HALO TIBO ANALOGS
PARKER, KA
COBURN, CA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (01): : 97 - 100
[39] PHASE-TRANSFER NUCLEOPHILIC AROMATIC-SUBSTITUTION OF CR(CO)3-COMPLEXED DICHLOROBENZENES WITH ALCOHOLS
ALEMAGNA, A
BALDOLI, C
DELBUTTERO, P
LICANDRO, E
MAIORANA, S
[J]. GAZZETTA CHIMICA ITALIANA, 1985, 115 (10): : 555 - 559
[40] ELECTROPHILIC AROMATIC-SUBSTITUTION .4. A KINETIC-STUDY OF THE FRIEDEL-CRAFTS BENZYLATION REACTION IN EXCESS AROMATIC
DEHAAN, FP
COVEY, WD
EZELLE, RL
MARGETAN, JE
PACE, SA
SOLLENBERGER, MJ
WOLF, DS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (21): : 3954 - 3958

← 1 2 3 4 5 →