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1.
Marvin L. Tedjamulia Yoshinori Tominaga Raymond N. Castle Milton L. Lee 《Journal of heterocyclic chemistry》1983,20(4):861-866
The synthesis of benzo[b]phenanthro[2, 3-d]thiophene ( 5 ), benzo[b]phenanthro[4, 3-d]thiophene ( 6 ), benzo-[b]phenanthro[2, 1-d]thiophene ( 9 ), benzo[b]phenanthro[3, 2-d]thiophene ( 14a ), anthra[1, 2-b]benzo[d]thiophene ( 24 ), anthra[2, 3-b]benzo[d]thiophene ( 29 ) and anthra[2, 1-b]benzo[d]thiophene ( 30 ) is described as well as the preparation of 13-methylbenzo[b]phenanthro[3, 2-d]thiophene ( 14b ). 相似文献
2.
The syntheses of the K-oxides and K-imine derivatives of benzo[b]phenanthro[2,3-d]thiophene and benzo-[b]phenanthro[3,2-d]thiophene are described. The parent hydrocarbons 1 and 2 were oxidized with osmium tetroxide and sodium metaperiodate, and the dialdehydes 12 and 18 so formed, cyclized to the corresponding epoxides 1a,12b-dihydrobenz[b]oxireno[9,10]phenanthro[2,3-d]thiophene ( 7 ) and 1a,12b-dihydrobenz-[b]oxireno[9,10]phenanthro[3,2-d]thiophene ( 13 ). Reaction of the oxiranes with sodium azide gave mixtures of azido-alcohols that, in turn, were transformed to the thiaarene imines 1a,12b-dihydro-1H-benz[b]azirino-[9,10]phenanthro[2,3-d]thiophene ( 8 ) and 1a,12b-dihydro-1H-benz[b]azirino[9,10]phenanthro[3,2-d]thiophene ( 14 ), respectively, with the aid of tri-n-butylphosphine. 相似文献
3.
Yoshinori Tominaga Milton L. Lee Raymond N. Castle 《Journal of heterocyclic chemistry》1981,18(5):967-972
All isomers of the parent anthra[b]thiophenes and benzo[b]naphtho[d]thiophenes, namely anthra[2,3-b]thio-phene, anthra[2,1-b]thiophene, anthra[1,2-b]thiophene, benzo[b]naphtho[2,3-d]thiophene, benzo[b]naphtho[2,1-d]thiophene and benzo[b]naphtho[1,2-d]thiophene were synthesized using a new procedure. 相似文献
4.
John G. Stuart Michael J. Quast Gary E. Martin Vincent M. Lynch Stanley H. Simonsen Milton L. Lee Raymond N. Castle Jerry L. Dallas Boban K. John LeRoy F. Johnson 《Journal of heterocyclic chemistry》1986,23(4):1215-1234
Syntheses of benzo[3,4]phenanthro[1,2-b]thiophene, benzo[3,4]phenanthro[2,1-b]thiophene and their 1-methyl analogs are reported as potential constituents of solvent refined coal liquids and for mutagenicity testing. The attempted synthesis of the 13-methyl analogs which gave the 11-methyl isomers is also described. Total assignments of the 1H- and 13C-nmr spectra based on long range optimized heteronuclear protoncarbon two-dimensional chemical shift correlation are reported. Carbon assignments obtained for benzo[3,4]-phenanthro[1,2-b]thiophene using this approach were confirmed with a 125 MHz 13C–13C INADEQUATE spectrum. X-Ray crystal structures were determined for benzo[3,4]phenanthro[1,2-b]thiophene and 1-methyl-benzo[3,4]phenanthro[2,1-b]thiophene. Both molecules were helically distorted from planarity. Close intramolecular contacts between the bay region H1–H13 and ClMe-H13 of 2.03 and 2.28 Å, respectively, were responsible for the distortions. There were no close intermolecular contacts of <3.5Å. both molecules refined to an R value of <0.05. 相似文献
5.
Masatomo Iwao Milton L. Lee Raymond N. Castle 《Journal of heterocyclic chemistry》1980,17(6):1259-1264
All isomers of the parent phenanthro[b]thiophenes, namely, phenanthro[1,2-b]thiophene, phenanthro-[2,1-b]thiophene, phenanthro[2,3-b]thiophene, phenanthro[3,4-b]thiophene, phenanthro[3,4-b]thiophene, phenanthro[4,3-b]thiophene and phenanthro[9,10-b]thiophene have been synthesized. 相似文献
6.
Hirotaka Kudo Marvin L. Tedjamulia Raymond N. Castle Milton L. Lee 《Journal of heterocyclic chemistry》1984,21(1):185-192
We describe the synthesis of thieno[2,3-c]dibenzothiophene ( 6 ), thieno[3,2-c]dibenzothiophene ( 10 ), thieno-[3,2-a]dibenzothiophene ( 14 ), thieno[2,3-a]dibenzothiophene ( 16 ), benzo[1,2-b:4,3-b]bisbenzo[b]thiophene ( 18 ), benzo[1,2--6:3,4-b]bisbenzo[b]thiophene ( 20 ), benzo[2,1--6:3,4-b]bisbenzo[b]thiophene ( 22 ), benzo[1,2-b:3,4-g]bisbenzo[b]thiophene ( 27 ), benzo[1,2-b:4,3-e]bisbenzo[b]thiophene ( 29 ), benzo[2,1--6:3,4-g]bisbenzo[b]thiophene ( 36 ), benzo[2,1--6:4,3-e]bisbenzo[b]thiophene ( 38 ), benzo[1,2--6:4,3-g]bisbenzo[b]thiophene ( 41 ), benzo[1,2-b:4,5-g]bisbenzo[b]thiophene ( 42 ), benzo[1,2-b:3,4-e]bisbenzo[b]thiophene ( 44 ) and benzo-[1,2-b:5,4-e]bisbenzo[b]thiophene ( 45 ). 相似文献
7.
Zusammenfassung Intramolekulare Cyclisierungsreaktionen von 3-Phenyl-benzo[b]thiophen-2-carbonsäurechlorid und von 2-Phenyl-benzo[b]thiophen-3-carbonsäurechlorid lieferten 6-Oxo-6H-benz[b]indeno[1,2-d]thiophen bzw. 10-Oxo-10H-benz[b]indeno[2,1-d]thiophen.
3. Mitt.:F. Sauter, Mh. Chem.99, 2100 (1968). 相似文献
Contributions to the chemistry of sulfur containing heterocycles, IV.: 6H-Benzo[b]indeno[1,2-d]thiophene and 10H-benzo-[b]indeno[1,2-d]thiophene
Intramolecular cyclization reactions of 3-phenyl-benzo[b]thiophene-2-carbonyl chloride and of 2-phenyl-benzo[b]-thiophene-3-carbonyl chloride gave 6-oxo-6H-benz[b]indeno-[1,2-d]thiophene and 10-oxo-10H-benz[b]indeno[2,1-d]thiophene, respectively.
3. Mitt.:F. Sauter, Mh. Chem.99, 2100 (1968). 相似文献
8.
Kazuhiro Maruyama Tetsuo Otsuki Kiichiro Mitsui Masahiro Tojo 《Journal of heterocyclic chemistry》1980,17(4):695-700
Anthra[2,1-b]furan, anthra[2,1-b]benzo[d]furan, anthra[2,1-b]thiophene, anthra[1,2-b]thiophene, anthra[2,1-b]benzo[d]thiophene, anthra[2,1-b]pyrrole and naphtho[2,3-c]carbazole derivatives were synthesized in fairly good yields by a one-pot photocycloaddition reaction of 2,3-disubstituted 1,4-naphthoquinone with 1,1-diarylethylene. This is the first reported synthesis of these aromatic compounds. 相似文献
9.
L. H. Klemm Michael P. Stevens Long K. Iran John Sheley 《Journal of heterocyclic chemistry》1988,25(4):1111-1116
Regioselectivity occurs in the sulfur-bridging reactions of 2,2′-binaphthyl (1) and 1-(2-naphthyl)cyclohexene (7) by means of hydrogen sulfide and a chromia-alumina-magnesia catalyst (designated I) in a flow apparatus at 550°. Thus, 1 gives a higher yield (6.1%) of dinaphtho[1,2–6:2′,l'-d]thiophene from 1,1′-bridging than of dinaphtho[1,2-b:2′,3′-d]thiophene (3.4%) from l,3′-bridging. No product expected from 3,3′-bridging was identified. Substrate 7 undergoes both dehydrogenation and bridging to yield 2-phenylnaphthalene (8%), benzo[b]naphtho[2,1-d]thiophene (9%) from alpha bridging, and benzo[b]naphtho[2,3-d]thiophene (3%) from beta bridging into the naphthalene ring. Exploratory studies showed that either sulfided catalyst I or a sulfided molybdenum( VI ) oxide-alumina-cobalt( II ) oxide catalyst ( II ) effects hydrodehalogenation of various monohalo- and polyhaloarenes (where halo, X, is chloro or bromo) at 450–550°. In the biphenyl, phenanthrene, naphthalene, and pyrene systems, halogen was lost either under sulfur-bridging conditions or under hydrogenolysis conditions, i.e. with methanol as a reactant. For every substrate the parent arene was isolated or identified as a reaction product. In selected experiments, acid HX was also identified in the effluent. Use of hydrogen sulfide as a reactant led to formation of dibenzothiophene and phenanthro[4,5-bcd]thiophene as main products in the biphenyl and phenanthrene systems, respectively; while use of methanol as a reactant gave small amounts of methyl bromide (for X = Br) and methylarenes. 相似文献
10.
The synthesis of both isomers of benzo[1,2]phenaleno[bc]thiophene namely, benzo[1,2]phenaleno[3,4-bc]-thiophene and benzo[1,2]phenaleno[4,3-bc]thiophene is described. 相似文献
11.
L. H. Klemm Sovitj Pou W. D. Detlefsen Clay Higgins Ross F. Lawrence 《Journal of heterocyclic chemistry》1984,21(5):1293-1296
1-Phenylnaphthalene undergoes sulfur bridging at 500° in the presence of hydrogen sulfide and a heterogeneous catalyst to produce benzo[b]naphtho[1,2-d]thiophene (13%). 3-Methylphenanthrene and 9-formylphenanthrene diethyl acetal ( 7b ) give sulfur bridging to produce phenanthro[4,5-bcd]thiophene, i.e. with loss of the ring substituent. Additionally, 7b hydrogenolyzes to 9-methylphenanthrene. With decadeuteriobiphenyl as a substrate, the dibenzothiophene formed, as well as the biphenyl recovered, is largely devoid of deuterium label. Confirmation that benzene and toluene react under sulfur-bridging conditions is presented. 相似文献
12.
Ram Pratap Yoshinori Tominaga Raymond N. Castle Milton L. Lee 《Journal of heterocyclic chemistry》1982,19(4):865-869
The synthesis of all the monomethyl derivatives of benzo[b]naphtho[2,3-d]thiophene is described. 相似文献
13.
Subodh Kumar Srinivasan Saravanan Peter Reuben Atul Kumar 《Journal of heterocyclic chemistry》2005,42(7):1345-1355
The present study describes the synthesis of phenanthro[3,4‐b]thiophene (3) , phenanthro[4,3‐b]thiophene (4) and its potential dihydrodiol metabolites, trans‐6,7‐dihydroxy‐6,7‐dihydrophenanthro[3,4‐b]thiophene (5) and trans‐8,9‐dihydroxy‐8,9‐dihydrophenanthro[3,4‐b]thiophene (6) , trans–6,7‐dihydroxy‐6,7‐dihydro‐phenanthro[4,3‐b]thiophene (7) and trans‐8,9‐dihydroxy‐8,9‐dihydrophenanthro[4,3‐b]thiophene (8) from Suzuki coupled intermediates. The UV spectra of these dihydrodiols are presented. These spectra are useful tools for identifying these dihydrodiols among unknown metabolites of 1 and 2 produced in vitro or in vivo. 相似文献
14.
The Synthesis of 2,3,4,5-1H-Tetrahydroimidazo[2,1-b]quinazolin-2,5-diones and analogous 2,3,4,5-1H-Tetrahydroimidazo[1,2-a]thieno[2,3-d] (or [3,2-d])-pyrimidin-2,5-diones The syntheses of various imidazo [2, 1-b]quinazolinediones and their thiophene analogs are described. 相似文献
15.
Gary E. Martin Stanford L. Smith W. John Layton M. Robert Willcott Masatomo Iwao Milton L. Lee Raymond N. Castle 《Journal of heterocyclic chemistry》1983,20(5):1367-1381
Two-dimensional nmr spectroscopy, by virtue of its second frequency domain which permits the segregation of spectral information along two frequency axes, considerably simplifies many assignment problems and facilitates others which may be impossible using conventional nmr methodology. A compound which falls into the latter category of assignment problem is phenanthro[1,2-b]thiophene. The assignment of the 1H- and 13C-nmr spectra of phenanthro[1,2-b]thiophene are, however, reported through the concerted application of two-dimensional nmr techniques. Experiments utilized in making the assignments included: auto-correlated homonuclear (COSY) two-dimensional spectroscopy; heteronuclear two-dimensional J-resolved spectroscopy; proton-carbon chemical shift correlation two-dimensional spectroscopy; and two-dimensional 13C-13C double quantum coherence spectroscopy. 相似文献
16.
Benzo[4,5]cyclohepta[1,2-b]quinoxaIine 2 , benzo[4,5]cyclohepta[1,2-b]pyrazine 3a and benzo[4,5]cyclohepta[1,2-b]quinoxaline 4 were prepared from 4,5-benzotropolone and 1,2-phenylenediamine, ethylenediamine and 1,2-diaminocyclohexane, respectively. Compound 3a was methylated to 3b . 相似文献
17.
Ram Pratap Yoshinori Tominaga Milton L. Lee Raymond N. Castle 《Journal of heterocyclic chemistry》1981,18(5):973-975
The synthesis of all the isomers of pyreno[b]thiophene namely, pyreno[1,2-b]thiophene, pyreno[2,1-b]thiophene and pyreno[4,5-b]thiophene is described. Their spectral characteristics are also discussed. 相似文献
18.
Yoshinori Tominaga Ram Pratap Raymond N. Castle Milton L. Lee 《Journal of heterocyclic chemistry》1982,19(4):859-863
All isomers of the monomethylbenzo[b]naphth[2,1-d]thiophenes were synthesized using photocyclization of 3-styrylbenzo[b]thiophenes. The 1-, 3-, 4-, and 5-methylbenzo[b]naphtho[2,1-d]thiophenes were synthesized by irradiation of the corresponding methylated 3-styrylbenzo[b]thiophenes which were prepared by the Wadsworth-Emmons reaction of diethyl benzo[b]thenylphosphonate with o-, m-, p-tolualdehyde and acetophenone. The 7-, 8-, 9- and 10-methylbenzo[b]naphtho[2,1-d]thiophenes were synthesized by decarboxylation of 7-, 8-, 9- and 10-methylbenzo[b]naphtho[2,1-d]thiophene-6-carboxylic acid with copper in quinoline. These carboxylic acids were prepared by photocyclization of the corresponding 2-(benzo[b]thiophen-3-yl)-3-phenylpropenoic acids which were prepared by the condensation of the methylated benzo[b]thiophene-3-ylacetic acids with benzaldehyde in the presence of triethylamine in acetic anhydride. 相似文献
19.
The synthesis of three novel polycyclic heterocyclic ring systems are reported via photocyclization. The specific final products in these ring systems are: phenanthro[9′,10′:4,5]thieno[2,3-c]quinoline ( 13 ), benzo[h]-phenanthro[9′,10′:4,5]thieno[2,3-c]quinoline ( 14 ), and benzo[f]phenanthro[9′,10′:4,5]thieno[2,3-c]quinoline ( 15 ). 相似文献
20.
Yoshinori Tominaga Raymond N. Castle Milton L. Lee 《Journal of heterocyclic chemistry》1982,19(5):1125-1130
Two pentacyclic thiophenes, benzo[4,5]phenaleno[1,9–6c]thiophene ( 1 ) and benzo[4,5]phenaleno[9,1-bc]-thiophene (2) were synthesized via the corresponding 3-methylphenanthro[2,1-b]thiophene (7) and 1-methylanthra[2,1–6]thiphene ( 19 ). 相似文献