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1.
Strategy to Construct Stair‐Shaped Partially Reduced Naphtho[1,2‐b]pyrano[2,3‐d]oxepines and Dinaphtho[1,2‐b,d]oxepines
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Sanjay K. Gautam Hardesh K. Maurya Ramendra Pratap Brijesh Kumar Abhinav Kumar Vishnu K. Tandon Vishnu Ji Ram 《Journal of heterocyclic chemistry》2016,53(6):2070-2078
A concise and efficient base‐induced synthesis of stair‐shaped, 4‐methylthio‐2‐oxo‐5,6‐dihydro‐2H‐naphtho[1,2‐b]pyran[2,3‐d]oxepine‐3‐carbonitriles ( 3 ) has been delineated by the reaction of 3,4‐dihydronaphtho[1,2‐b]oxepin‐5(2H)‐one ( 1 ) and methyl 2‐cyano‐3,3‐dimethylthioacrylate in DMSO using powdered KOH as a base at room temperature. Amination of 3 has been achieved by reaction with secondary amine in ethanol at reflux temperature to yield 4‐sec‐amino‐2‐oxo‐5,6‐dihydro‐2H‐naphtho[1,2‐b]pyran[2,3‐d]oxepine‐3‐carbonitriles ( 4 ). Reaction of 3 with aryl methyl ketone ( 5 ) in DMSO at room temperature using powdered KOH as a base produced stair‐shaped 5‐aryl‐7,8‐dihydro‐1,4‐dioxa‐2,3‐dioxodinaphtho[1,2‐b,d]oxepine ( 6 ) in good yields. However, reaction of 6‐aryl‐2H‐pyran‐2‐one‐3‐carbonitrile ( 8 ) with 3,4‐dihydronaphtho[1,2‐b]oxepin‐5(2H)‐one ( 1 ) did not give similar product, but in lieu 4‐aryl‐5,6‐dihydronaphtho[1,2‐b]oxepino[4,5‐b]pyran‐2‐ylidene)acetonitrile ( 9 ) was isolated and characterized. 相似文献
2.
Jiann‐Kuan Luo Maria‐Paz Cabal Ronald F. Federspiel Raymond N. Castle 《Journal of heterocyclic chemistry》2001,38(1):137-140
A previously unknown heterocyclic ring system, naphtho[2′,1′:4,5]thieno[2,3‐c]naphtho[2,1‐f]quinoline ( 14 ), was synthesized via oxidative photocyclization of 3‐chloro‐N‐(2‐phenanthryl)naphtho[1,2‐b]‐thiophene‐2‐carboxamide ( 9 ). Further elaboration of the lactam 10 yielded the unsubstituted ring system 14 . Structural confirmation of compound 14 was accomplished by a total assignment of its 1H and 13C nmr spectra utilizing the concerted two‐dimensional nmr spectroscopic methods. 相似文献
3.
Jiann-Kuan Luo Ronald F. Federspiel Raymond N. Castle 《Journal of heterocyclic chemistry》1996,33(3):923-926
The synthesis of two previously unknown polycyclic ring systems, benzo[h]naphtho[1′2′:4,5]-thieno[2,3-c]quinoline ( 1 ) and benzo[h]naphtho[1′,2′:4,5]thieno[2,3-c][1,2,4]triazolo[4,3-a]quinoline ( 2 ), was achieved via oxidative photocyclization of 1-chloro-N-(1-naphthyl)naphtho[2,1-b]thiophene-2-carboxamide ( 5 ). The total assignment of their 1H and 13C nmr spectra was determined by the concerted use of two-dimensional nmr methods. 相似文献
4.
A series of novel fused tetracyclic benzo[4,5]imidazo[1,2‐a]thiopyrano[3,4‐d]pyrimidin‐4(3H)‐one derivatives were synthesized via the reaction of aryl aldehyde, 2H‐thiopyran‐3,5(4H,6H)‐dione, and 1H‐benzo[d]imidazol‐2‐amine in glacial acetic acid. This protocol features mild reaction conditions, high yields and short reaction time. 相似文献
5.
Werner Andres Harald Günther Maria‐Eugenia Günther Heike Hausmann Günther Jikeli Henning vonPuttkamer Hans Schmickler Jier Niu‐Schwarz W.H.Eugen Schwarz 《Helvetica chimica acta》2001,84(6):1737-1755
The bonding situation in a series of biphenylene analogues – benzo[b]biphenylene and its dication, 4,10‐dibromobenzo[b]biphenylene, naphtho[2,3‐b]biphenylene and its dianion, benzo[a]biphenylene, (biphenylene)tricarbonylchromium, benzo[3,4]cyclobuta[1,2‐c]thiophene, benzo[3,4]cyclobuta[1,2‐c]thiophene 2‐oxide, benzo[3,4]cyclobuta[1,2‐c]thiophene 2,2‐dioxide, 4,10‐diazabenzo[b]biphenylene, biphenylene‐2,3‐dione, benzo[3,4]cyclobuta[1,2‐b]anthracene‐6,11‐dione, and 3,4‐dihydro‐2H‐benzo[3,4]cyclobuta[1,2]cycloheptene – where one of the two benzo rings of biphenylene is replaced by a different π‐system (B) was investigated on the basis of the NMR parameters of these systems. From the vicinal 1H,1H spin‐spin coupling constants, the electronic structure of the remaining benzo ring (A) is derived via the Q‐value method. It is found that increasing tendency of B to tolerate exocyclic double bonds at the central four‐membered ring of these systems favors increased π‐electron delocalization in the A ring. The analysis of the chemical shifts supports this conclusion. NICS (nucleus‐independent chemical shift) values as well as C,C bond lengths derived from ab initio calculations are in excellent agreement with the experimental data. The charged systems benzo[b]biphenylene dication and naphtho[2,3‐b]biphenylene dianion ( 7 2−) are also studied by 13C NMR measurements. The charge distribution found closely resembles the predictions of the simple HMO model and reveals that 7 2− can be regarded as a benzo[3,4]cyclobuta[1,2‐b]‐substituted anthracene dianion. It is shown that the orientation of the tricarbonylchromium group in complexes of benzenoid aromatics can be derived from the vicinal 1H,1H coupling constants. 相似文献
6.
Jiann-Kuan Luo Steven L. Castle Raymond N. Castle 《Journal of heterocyclic chemistry》1993,30(3):653-658
The synthesis of two previously unknown heterocyclic ring systems, namely benzo[h]naphtho[2′,1′:4,5]thi-eno[2,3-c]quinoline (1) and benzo[f]naphtho[2′,1:4,5]thieno[2,3-c]quinoline (2) was accomplished via photocyclization of the appropriate amides followed by chlorination and catalytic dechlorination. The total assignment of 1H and 13C nmr spectra of 2 was determined utilizing two-dimensional nmr methods, providing unequivocal structural proof of the two novel polycyclic ring systems. 相似文献
7.
Yoshinori Tominaga Lyle W. Castle Raymond N. Castle 《Journal of heterocyclic chemistry》1996,33(4):1319-1321
Photocyclization of the substituted 2-([1]benzothien-3-yl)-3-phenylpropenoic acids 3a-c in the presence of iodine and air in a benzene-cyclohexane mixture afforded a separable mixture of three compounds, benzo[b]naphtho[2,1-d]thiophene-6-carboxylic acids 4a-c , 6H-benzo[b]naphtho[2,3-d]thiopyran-6-ones 5a-c , and 10-methoxy-2-methyl-6H-benzo[b]naphtho[2,3-d]pyran-6-one ( 6 ). 相似文献
8.
Valery S. Tolkunov Igor F. Perepichka Vladimir I. Dulenko 《Journal of heterocyclic chemistry》2005,42(5):811-817
Reaction of 2‐acyl‐6‐methylbenzo[b]furan‐3‐acetic acids and their derivatives such as amides and esters with hydrazine does not give expected 1‐alkyl‐5H‐benzofuro[2,3‐e]diazepin‐4‐ones ones but results in 2‐amino‐7‐methyl‐2H‐benzo[4,5]furo[2,3‐c]pyridin‐3‐ones or (3‐R‐6‐methylbenzo[b]furan‐2‐yl)alkyl ketone azines. 相似文献
9.
Mechanism of the condensation reactions of methylglyoxal, phenylglyoxal and benzoylacetaldehyde with phenolic compounds have been discussed. It was observed that the reaction mechanisms changed depending on the type of the phenolic and also dicarbonyl compounds. While, methylglyoxal gave the angular methyl derivative of naphthofuraranonaphthofuran with 2‐naphthol, phenylglyoxal and its p‐chloro and p‐methoxy derivatives formed benzo[b]naphtho[2,1‐f]oxepine‐13‐ones. However, resorcinol behaved different and gave 2‐phenyl‐3‐(2,4‐dihydroxy)‐6‐hydroxy‐benzo[b]furans with phenylglyoxal derivatives. 2‐Phenyl‐4‐(2‐hydroxynaphmyl)‐4H‐naphtho[b]pyran was produced from the reaction of benzoylacetaldehyde and 2‐naphthol, but the reaction product was 3,9‐dihydroxy‐6‐phenyl‐6,12‐methano‐12H‐dibenzo[1,3]dioxocin when the same carbonyl compound reacted with resorcinol. 相似文献
10.
Kenji Sasaki Osamu Tokuda Takashi Hirota Jiann-Kuan Luo Ronald F. Federspiel Raymond N. Castle 《Journal of heterocyclic chemistry》1997,34(6):1829-1832
The polycyclic heterocyclic compound with a novel ring system, 15-chloro[1]benzothieno[2″,3″:3′,4′]-naphtho[1′,2′:4,5]thieno[2,3-c]quinoline was synthesized via photocyclization of 3-chloro-N-phenyl[1]-benzothieno[2′,3′:3,4]naphtho[2,1-b]fhiophene-2-carboxamide followed by chlorination with phosphorus oxychloride. The assignment of its 1H and 13C nmr spectra was accomplished by utilizing two-dimensional nmr methods. 相似文献
11.
Fathy Mohamad Abdel Aziz El‐Taweel 《Journal of heterocyclic chemistry》2005,42(5):943-946
Several new benzo[ij]pyrano[2,3‐b]quinolizine‐8‐ones 5 and 4H‐pyrano[2,3‐b]pyridine 8 derivatives were synthesized from 4‐hydroxyquinolines 1 . Reacting 3‐acetyl‐4‐hydroxy‐1‐phenyl‐1H‐quinoline‐2‐one with dimethylformamide dimethylacetal afforded 3‐(3‐Dimethylarnino‐acryloyl)‐4‐hydroxy‐1‐phenyl‐1H‐quinolin‐2‐one 9 . This reacted with hippuric acid and diethyl 3‐oxoglutarate to give 2H‐pyran‐2‐one 13 and pyranopyridoquinoline 17 respectively. 相似文献
12.
One‐Pot Three‐Component Synthesis of Benzo[f]thiopyrano[3,4‐b]quinolin‐11(8H)‐one Derivatives
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Chenxia Yu Honghong Zhang Changsheng Yao Tuanjie Li Bingbin Qin Jun Lu Donglin Wang 《Journal of heterocyclic chemistry》2014,51(3):702-705
A series of novel benzo[f]thiopyrano[3,4‐b]quinolin‐11(8H)‐one derivatives were synthesized via the reaction of aryl aldehyde, 2H‐thiopyran‐3,5(4H,6H)‐dione, and β‐naphthylamine in glacial acetic acid. This protocol features mild reaction conditions, high yields, and short reaction time. 相似文献
13.
Jiann-Kuan Luo Ronald F. Federspiel Raymond N. Castle 《Journal of heterocyclic chemistry》1997,34(5):1597-1601
Photocyclization of 3-chloro-N-(3-phenanthryl)thieno[2,3-b]thiophene-2-carboxamide ( 5 ) yielded only one of the two possible structural isomers, thieno[3′,2′:4,5]thieno[2,3-c]naphtho[1,2-f]quinolin-6(5H)-one ( 6 ), which was further elaborated to afford the unsubstituted ring system 10 , its triazole 11 and tetrazole 12 . The structural confirmation of 10 was achieved by the total assignment of its 1H and 13C nmr spectra by the concerted utilization of two-dimensional nmr spectroscopic methods. 相似文献
14.
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
15.
Djamila Hikem‐Oukacha Maamar Hamdi Artur M. S. Silva Rachedi Yahia 《Journal of heterocyclic chemistry》2011,48(1):63-68
3‐(Bromoacetyl)‐4‐hydroxy‐6‐methyl‐2H‐pyran‐2‐one was synthesized by the reaction of dehydroacetic acid (DHAA) with bromine in glacial acetic acid. Novel heterocyclic products were synthesized from the reaction of bromo‐DHAA with alkanediamines, phenylhydrazines, ortho‐phenylenediamines, and ortho‐aminobenzenethiol. The obtained new products 3‐(2‐N‐substituted‐acetyl)‐4‐hydroxy‐6‐methyl‐2H‐pyran‐2‐ones, 4‐hydroxy‐3‐[1‐hydroxy‐2‐(2‐phenylhydrazinyl)vinyl]‐6‐methyl‐2H‐pyran‐2‐one, 1‐(2,4‐dinitrophenyl)‐7‐methyl‐2,3‐dihydro‐1H‐pyrano[4,3‐c]pyridazine‐4,5‐dione, 3‐(3,4‐dihydroquinoxalin‐2‐yl)‐4‐hydroxy‐6‐methyl‐2H‐pyran‐2‐one/3‐(3,4‐dihydroquinoxalin‐2‐yl)‐6‐methyl‐2H‐pyran‐2,4(3H)‐dione, 6‐methyl‐3‐(3,4‐dihydroquinoxalin‐2‐yl)‐2H‐pyran‐2,4(3H)‐dione, and (E)‐3‐(2H‐benzo[b][1,4]thiazin‐3(4H)‐ylidene)‐6‐methyl‐2H‐pyran‐2,4(3H)‐dione were fully characterized by IR, 1H and 13C NMR, and mass spectra. J. Heterocyclic Chem., 2011. 相似文献
16.
Alkyl 2‐[2‐ethoxycarbonyl‐2‐(2‐pyridinyl)ethenyl]amino‐3‐dimethylaminopropenoates 3 and 4 were transformed with C‐and N‐nucleophiles into β‐heteroaryl‐α,β‐didehydro‐α‐amino acid derivatives 13 ‐ 16 , substituted 3‐amino‐4H‐quinolizin‐4‐one 17, 2H,5H‐benzo[b]pyran‐2,5‐dione 18 and 19 , 2H,5H‐pyrano[4,3‐b]pyran‐2,5‐dione 20 , 2H,5H‐pyrano[3,2‐c]benzo[b]pyran‐2,5‐dione 21 , 2H‐1‐benzopyran‐2‐one 22 and 24 , pyrido[l,2‐a]pyrimidin‐4‐one 31–34 and 39 derivatives, and N‐heteroaryl‐1H‐imidazole‐4‐carboxylates 37 and 38 . 相似文献
17.
Albert Lévai József Jekő Tímea Gondos András Simon Gábor Tóth 《Journal of heterocyclic chemistry》2007,44(6):1453-1458
18.
Jiann‐Kuan Luo Maria P. Cabal Ronald F. Federspiel Raymond N. Castle 《Journal of heterocyclic chemistry》2000,37(4):997-1001
Photocyclization of 3‐chloro‐N‐(9‐phenanthryl)benzo[b]‐thiophene‐2‐carboxamide ( 3 ) and 3‐chloro‐N‐(9‐phenanthryl)‐naphtho[1,2‐b]thiophene‐2‐carboxamide ( 10 ) yielded dibenzo[f,h]benzothieno[2,3‐c]‐quinolin‐10(9H)‐one ( 4 ) and dibenzo[f,h]naphtho[2′,1′:4,5]thieno[2,3‐c]quinolin‐10(9H)‐one ( 11 ), respectively. Further elaboration of the lactams provided three novel unsubstituted new ring systems. 相似文献
19.
Two previously unknown heterocyclic ring systems, namely, [1]benzothieno[2,3-c]naphtho[2,1-f]quinoline ( 4 ) and [1]benzothieno[2,3-c]naphtho[1,2-g]quinoline ( 5 ) were synthesized via photocyclization of 3-chloro-N-(2-phenanthryl)benzo[b]thiophene-2-carboxamide ( 8 ) followed by chlorination and dechlorination. The total assignment of their 1H- and 13C-nmr spectra was determined by utilizing inverse-detected HMQC and HMBC two-dimensional nmr spectroscopic methods. 相似文献
20.
《合成通讯》2013,43(7):1265-1275
Abstract 4‐Mercapto‐6‐methyl‐2‐pyrone was alkylated with different allylic and propargylic halides under phase transfer catalyzed condition in the presence of TBAB or BTEAC catalyst in chloroform–aqueous NaOH (1%) at room temperature. The S‐alkylated thiopyran‐2‐ones were then refluxed in quinoline or in chlorobenzene to give 4‐chloromethylthiopyrano[2,3‐b]pyran‐2‐one and 4‐hydroxymethylthiopyrano[2,3‐b]pyran‐2‐one or several thieno[2,3‐b]pyran‐2‐ones. 相似文献