CHEMISTRY OF HETEROCYCLIC-COMPOUNDS .136. 1,3,5-TRI[2,6]PYRIDACYCLOHEXAPHANE-2,4,6-TRIONE KETALS - SYNTHESIS, STRUCTURAL-ANALYSIS, AND COMPLEXATION

被引：15

作者：

NEWKOME, GR ^{[1
]}

JOO, YJ ^{[1
]}

EVANS, DW ^{[1
]}

FRONCZEK, FR ^{[1
]}

BAKER, GR ^{[1
]}

机构：

[1] LOUISIANA STATE UNIV,DEPT CHEM,BATON ROUGE,LA 70803

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 22期

关键词：

D O I：

10.1021/jo00309a015

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis, molecular distortions, and chemical behavior of l,3,5-tri[2,6]pyridacyclohexaphane-2,4,6-trione ketals are described. The electron-deficient nature of the carbonyl bridges was confirmed by the facile addition of protic solvent to generate a stable hemiketal. The bridging methylene moiety of the carbonyl precursor exhibited novel chemical behavior, which results in a facile dimerization of a radical intermediate. X-ray structural analyses of the ketals and dimers afforded insight into the molecular deviations caused by changing the bond angles of the bridging carbon atoms. © 1990, American Chemical Society. All rights reserved.

引用

页码：5714 / 5719

页数：6

共 11 条

[1] CONVENIENT SYNTHESIS AND STRUCTURAL ASPECTS OF 1,3,5-TRI[2,6]PYRIDACYCLOHEXAPHANE-2,4,6-TRIONE AND PRECURSORS
NEWKOME, GR
JOO, YJ
THERIOT, KJ
FRONCZEK, FR
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (19) : 6074 - 6075
[2] SYNTHESIS OF A NOVEL MACROCYCLIC SYSTEM - 1,3,5-TRI[2,6]PYRIDACYCLOHEXAPHANE-2,4,6-TRIONE
NEWKOME, GR
SAUER, JD
MATTSCHEI, PK
NAYAK, A
HETEROCYCLES, 1978, 9 (11) : 1555 - 1560
[3] UREAS IN ORGANIC-SYNTHESIS .10. SYNTHESIS OF PERHYDRO-2-PHENYL-1,3,5-TRIAZINE-4,6-DIONE AND 1,3,5-TRI(METHYLTHIOMETHYL)1,3,5-TRIAZINO-2,4,6-TRIONE VIA INTERACTION OF BENZALDEHYDE WITH UREA OR FROM BENZYLINENOBISUREA UNDER THE ACTION OF DIMETHYL-SULFOXIDE
BAKIBAEV, AA
ZHURNAL ORGANICHESKOI KHIMII, 1994, 30 (11): : 1686 - 1687
[4] RING TRANSFORMATIONS OF HETEROCYCLIC-COMPOUNDS .3. PROPAN-1,3-DIONES FROM 2,4,6-TRIARYLPYRYLIUM SALTS AND 1,5-DIPHENYL-PENTAN-1,3,5-TRIONE
ZIMMERMANN, T
JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG, 1993, 335 (05): : 479 - 481
[5] STUDIES ON SYNTHESES OF HETEROCYCLIC-COMPOUNDS .511. STUDIES ON SYNTHESES OF ANALGESICS .36. SYNTHESIS OF 1,2,3,4,5,6-HEXAHYDRO-2,6-METHANO-6-PHENYL-2-BENZAZOCINE
KAMETANI, T
AOYAMA, T
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1973, 10 (03) : 291 - 295
[6] Synthesis, NMR, FT-IR, X-ray structural characterization, DFT analysis and isomerism aspects of 5-(2,6-dichlorobenzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione
Barakat, Assem
Al-Najjar, Hany J.
Al-Majid, Abdullah Mohammed
Soliman, Saied M.
Mabkhot, Yahia Nasser
Shaik, Mohammed Rafi
Ghabbour, Hazem A.
Fun, Hoong-Kun
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2015, 147 : 107 - 116
[7] STUDIES ON SYNTHESES OF ANALGESICS .31. SYNTHESIS OF 1,2,3,4,5,6-HEXAHYDRO-3-METHYL-6-PHENYL-2,6-METHANO-2,3-BENZO[G] DIAZOCINE [STUDIES ON SYNTHESES OF HETEROCYCLIC-COMPOUNDS .479.
KAMETANI, T
HIIRAGI, M
KIGASAWA, K
AOYAMA, T
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1972, 9 (05) : 1061 - &
[8] SYNTHETIC STUDIES ON CHEMISTRY OF POLYENE COMPOUNDS .46. COMPLETE SYNTHESIS OF RAC-ETHYL ETHER (2E,4E,6E)-5-METHYL-7-(2,6-DIMETHYL-6-ETHOXYCARBONYL-3-OXO-1-CYCLOHEXENE-1-IL)-2,4,6-HEPTATRIENIC ACID
ZHIDKOVA, TA
BEKKER, AR
VAKULOVA, LA
SAMOKHVALOV, GI
ZHURNAL ORGANICHESKOI KHIMII, 1984, 20 (08): : 1678 - 1683
[9] SYNTHETIC INVESTIGATIONS ON CHEMISTRY OF POLYENE COMPOUNDS .49. SYNTHESIS OF RAC-(2E,4E)-3-METHYL-5-(2,6-DIMETHYL-6-ETHOXYCARBONYL-3-OXO-1-CYCLOHEXEN-1-YL)-2,4-PENTADIENAL AND RAC-(2E,4E,6E)-5-METHYL-7-(2,6-DIMETHYL-6-ETHOXYCARBONYL-3-OXO-1-CYCLOHEXEN-1-YL)-2,4,6-HEPTATRIENAL AND THEIR DERIVATIVES WITH DIMEDONEC
ZHIDKOVA, TA
STASHINA, GA
BOGDANOV, VS
VAKULOVA, LA
SAMOKHVALOV, GI
ZHURNAL ORGANICHESKOI KHIMII, 1985, 21 (08): : 1653 - 1658
[10] STUDIES ON SYNTHESES OF ANALGESICS .39. SYNTHESIS OF 1,2,3,4,5,6-HEXAHYDRO-8-HYDROXY-2,6-METHANO-3,6,11-TRIMETHYL-2,3-BENZO[G]DIAZOCINE AND 1,2,3,4,5,10,11,12-OCTAHYDRO-7-HYDROXY-1,5-DIMETHYLPYRIDAZINO[2,3-B]ISOQUINOLINE [STUDIES ON SYNTHESES OF HETEROCYCLIC-COMPOUNDS .61. (2)I
KAMETANI, T
KIGASAWA, K
HIIRAGI, M
WAKISAKA, K
WAGATSUMA, N
KUSAMA, O
URYU, T
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1973, 10 (06) : 999 - 1005

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