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

[41] STRUCTURAL EFFECTS ON REACTIVITY OF CARBON RADICALS IN HOMOLYTIC AROMATIC-SUBSTITUTION .4. NUCLEOPHILICITY OF BRIDGEHEAD RADICALS
FIORENTINO, M
TESTAFERRI, L
TIECCO, M
TROISI, L
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1977, (01): : 87 - 93
[42] FRIEDEL-CRAFTS ACYLATION OF ACETYLENES .4. ON THE NON SELECTIVITY OF ACYLVINYL CATIONS IN AROMATIC-SUBSTITUTION
MANOIU, D
MANOIU, M
DINULESCU, IG
AVRAM, M
[J]. REVUE ROUMAINE DE CHIMIE, 1984, 29 (11-1) : 857 - 860
[43] INTERMEDIATES IN NUCLEOPHILIC AROMATIC SUBSTITUTION .6. KINETIC EVIDENCE OF INTRAMOLECULAR HYDROGEN BONDING IN MEISENGEIMER COMPLEXES
BERNASCONI, CF
[J]. JOURNAL OF PHYSICAL CHEMISTRY, 1971, 75 (23): : 3636 - +
[44] PREPARATION OF TERT-BUTYL 4-N-(OMEGA-AMINOALKYL)AMINOBENZOATES BY NUCLEOPHILIC AROMATIC-SUBSTITUTION
KALINDJIAN, SB
SMITH, RAG
[J]. SYNLETT, 1991, (11) : 803 - 804
[45] A SURPRISING EFFECT OF LEAVING GROUP ON THE NUCLEOPHILIC AROMATIC-SUBSTITUTION REACTION CATALYZED BY 4-CHLOROBENZOYL-COA DEHALOGENASE
CROOKS, GP
COPLEY, SD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (14) : 6422 - 6423
[46] Synthesis of 1H-quinazoline-4-ones using intramolecular aromatic nucleophilic substitution
Bowman, WR
Heaney, H
Smith, PHG
[J]. ARKIVOC, 2003, : 434 - 442
[47] MECHANISMS FOR REACTIONS OF HALOGENATED COMPOUNDS .3. VARIATION IN ACTIVATING INFLUENCE OF HALOGEN SUBSTITUENTS IN NUCLEOPHILIC AROMATIC-SUBSTITUTION
CHAMBERS, RD
CLOSE, D
WILLIAMS, DLH
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1980, (05): : 778 - 780
[48] CATALYSIS IN AROMATIC NUCLEOPHILIC-SUBSTITUTION .4. REACTIONS OF PIPERIDINE WITH 2-METHOXY-3-NITROTHIOPHEN IN BENZENE
CONSIGLIO, G
NOTO, R
SPINELLI, D
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1979, (02): : 222 - 223
[49] COMPETITIVE NUCLEOPHILIC AROMATIC-SUBSTITUTION AND PALLADIUM-CATALYZED ALKOXYCARBONYLATION OF (SUBSTITUTED CHLOROARENE)CR(CO)(3) COMPLEXES
CARPENTIER, JF
FINET, E
CASTANET, Y
BROCARD, J
MORTREUX, A
[J]. TETRAHEDRON LETTERS, 1994, 35 (28) : 4995 - 4998
[50] Nucleophilic aromatic substitution of methyl 3-nitropyridine-4-carboxylate
Holt, J
Tjosås, F
Bakke, JM
Fiksdahl, A
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2004, 41 (06) : 987 - 989

← 1 2 3 4 5 →