Polycyclic fused phenanthridines: An alternative approach from benzotriazoles

被引：23

作者：

Katritzky, AR ^{[1
]}

Du, WH ^{[1
]}

Matsukawa, Y ^{[1
]}

Ghiviriga, I ^{[1
]}

Denisenko, SN ^{[1
]}

机构：

[1] Univ Florida, Dept Chem, Ctr Heterocycl Cpds, Gainesville, FL 32611 USA

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 1999年 / 36卷 / 04期

关键词：

D O I：

10.1002/jhet.5570360417

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe an alternative approach to polycyclic phenanthridines (7) and some of their analogues using conditions much milder than those previously reported. The procedure includes the generation of a benzotriazole stabilized carbanion, oxidation of the resulting anion to a radical, and elimination of nitrogen followed by ring closure to produce phenanthridines.

引用

页码：927 / 932

页数：6

共 15 条

[1] H-1 AND C-13 ASSIGNMENTS FROM SENSITIVITY-ENHANCED DETECTION OF HETERONUCLEAR MULTIPLE-BOND CONNECTIVITY BY 2D MULTIPLE QUANTUM NMR
BAX, A
SUMMERS, MF
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (08) : 2093 - 2094
[2] SELECTION OF COHERENCE-TRANSFER PATHWAYS IN NMR PULSE EXPERIMENTS
BODENHAUSEN, G
KOGLER, H
ERNST, RR
[J]. JOURNAL OF MAGNETIC RESONANCE, 1984, 58 (03) : 370 - 388
[3] COHERENCE TRANSFER BY ISOTROPIC MIXING - APPLICATION TO PROTON CORRELATION SPECTROSCOPY
BRAUNSCHWEILER, L
ERNST, RR
[J]. JOURNAL OF MAGNETIC RESONANCE, 1983, 53 (03) : 521 - 528
[4] Antitumour polycyclic acridines .1. Synthesis of 7H-pyrido- and 8H-quino-[4,3,2-kl]acridines by Graebe-Ullmann thermolysis of 9-(1,2,3-triazol-1-yl)acridines: application of differential scanning calorimetry to predict optimum cyclisation conditions
Hagan, DJ
GimenezArnau, E
Schwalbe, CH
Stevens, MFG
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (18): : 2739 - 2746
[5] NITROSATION OF DERIVATIVES OF HYDRAZINES .9. NOVEL OXIDATIVE C-N-COUPLING OF INDAZOLES AND BENZOTRIAZOLES WITH CYCLOHEPATRIENE, DIPHENYLMETHANE AND TRIPHENYLMETHANE DERIVATIVES
HANEFELD, W
HUNZ, I
[J]. ARCHIV DER PHARMAZIE, 1993, 326 (06) : 323 - 329
[6] Syntheses of β,β-diarylvinyl phenyl ketones by benzotriazole-mediated tandem coupling-elimination
Katritzky, AR
Denisenko, SN
Oniciu, DC
Ghiviriga, I
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (10) : 3450 - 3453
[7] Benzotriazole-mediated conversions of para-H-substituted pyrylium, benzo[b]pyrylium, and xanthylium salts into para-position functionalized derivatives (an indirect electrophilic substitution of electron-deficient heteroaromatics)
Katritzky, AR
Czerney, P
Levell, JR
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (23) : 8198 - 8200
[8] Radical mediated synthesis of 6-arylphenanthridines via benzotriazole ring-opening
Katritzky, AR
Yang, BZ
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1996, 33 (03) : 607 - 610
[9] IMPROVED FREQUENCY-SELECTIVITY IN NUCLEAR OVERHAUSER EFFECT DIFFERENCE SPECTROSCOPY
KINNS, M
SANDERS, JKM
[J]. JOURNAL OF MAGNETIC RESONANCE, 1984, 56 (03) : 518 - 520
[10] UBER PSEUDOBASEN, .5. VERSUCHE IN DER ACRIDINIUM-REIHE
KROHNKE, F
HONIG, HL
[J]. CHEMISCHE BERICHTE-RECUEIL, 1957, 90 (10): : 2215 - 2225

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