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1.
Thomas Kappe Peter Roschger Birgit Schuiki Wolfgang Stadlbauer 《Journal of heterocyclic chemistry》2003,40(2):297-302
2‐Methyl‐3H‐indoles 1 cyclize with two equivalents of ethyl malonate 2 to form 4‐hydroxy‐11H‐benzo[b]pyrano[3,2‐f]indolizin‐2,5‐diones 3, whereas 2‐mefhyl‐2,3‐dihydro‐1H‐indoles 9 give under similar conditions regioisomer 8‐hydroxy‐5‐methyl‐4,5‐dihydro‐pyrrolo[3,2,1‐ij]pyrano[3,2‐c]quinolin‐7,10‐diones 10 . The pyrone rings of 3 and 9 can be cleaved either by alkaline hydrolysis to give 7‐acetyl‐8‐hydroxy‐10H‐pyrido[1,2‐a]indol‐6‐ones 4 or 5‐acetyl‐6‐hydroxy‐2‐methyl‐1,2‐dihydro‐4H‐pyrrolo‐[3,2,1‐ij]quinolin‐4‐ones 11 , respectively. Chlorination of 3 and 9 with sulfurylchloride gives under subsequent ring opening 7‐dichloroacetyl‐8‐hydroxy‐10H‐pyrido[1,2‐a]indol‐6‐ones 5 or 5‐dichloracetyl‐6‐hydroxy‐2‐methyl‐1,2‐dihydro‐4H‐pyrrolo[3,2,1‐ij]quinolin‐4‐ones 12 . The dichloroacetyl group of 5 can be reduced with zinc to 7‐acetyl‐8‐hydroxy‐10H‐pyrido[1,2‐a]indol‐6‐ones 7. Treatment of the acetyl compounds 4, 7 and 11 with 90% sulfuric acid cleaves the acetyl group and yields 8‐hydroxy‐10H‐pyrido[1,2‐a]‐indol‐6‐ones 6 and 8 , and 6‐hydroxy‐2‐methyl‐1,2‐dihydro‐4H‐pyrrolo[3,2,1‐ij]quinolin‐4‐ones 13 . Reaction of dichloroacetyl compounds 12 with sodium azide yields 6‐hydroxy‐2‐methyl‐5‐(1H‐tetrazol‐5‐ylcarbonyl)‐1,2‐dihydro‐4H‐pyrrolo[3,2,1‐ij]quinolin‐4‐ones 14 via intermediate geminal diazides. 相似文献
2.
Afsaneh Feiz Ghazaleh Imani Shakibaei Zahra Yasaei Hamid Reza Khavasi Ayoob Bazgir 《Helvetica chimica acta》2011,94(9):1628-1637
A new four‐component synthesis of spiro[4H‐indeno[1,2‐b]pyridine‐4,3′‐[3H]indoles] and spiro[acenaphthylene‐1(2H),4′‐[4H‐indeno[1,2‐b]pyridines] by the reaction of indane‐1,3‐dione, 1,3‐dicarbonyl compounds, isatins (=1H‐indole‐2,3‐diones) or acenaphthylene‐1,2‐dione, and AcONH4 in refluxing toluene in the presence of a catalytic amount of pyridine is reported. 相似文献
3.
Ahmed I. Khodair 《Journal of heterocyclic chemistry》2002,39(6):1153-1160
Various 5H‐thiazolo[2,3‐b]quinazoline‐3,5[2H]‐diones (7a,b), 2‐arylidene‐5H‐thiazolo[2,3–b]quin‐azoline‐3,5[2H]‐diones ( 9a‐o ) and 2‐arylidene‐5H‐thiazolo[2,3‐b]benzoquinazoline‐3,5[2H]‐diones ( 12a,b ) have been synthesized via simple and efficient methods. 相似文献
4.
Jaime Portilla Jairo Quiroga Justo Cobo John N. Low Christopher Glidewell 《Acta Crystallographica. Section C, Structural Chemistry》2007,63(8):o458-o461
In both 2,5‐dimethyl‐6,7‐dihydrobenzo[h]pyrazolo[1,5‐a]quinazoline, C16H15N3, (I), and 2‐tert‐butyl‐5‐methyl‐6,7‐dihydrobenzo[h]pyrazolo[1,5‐a]quinazoline, C19H21N3, (II), which crystallizes with Z′ = 2 in the space group P, the non‐aromatic carbocyclic rings adopt screw‐boat conformations. The molecules of (I) are linked into chains of rings by a combination of C—H...N and C—H...π(arene) hydrogen bonds, while in (II) there are no hydrogen bonds of any kind. 相似文献
5.
Amrah Nouri Ahmad Poursattar Marjani Jabbar Khalafy 《Journal of heterocyclic chemistry》2019,56(10):2912-2921
A new series of benzo[g]thiazolo[2,3‐b]quinazolin‐4‐ium and benzo[g]benzo[4,5]thiazolo[2,3‐b]quinazolin‐14‐ium hydroxide derivatives have been synthesized by the one‐pot, three‐component reaction of aryl glyoxal monohydrates, 2‐hydroxy‐1,4‐naphthoquinone, and 2‐aminothiazole or 2‐aminobenzothiazole in the presence of triethylamine and p‐toluenesulfonic acid as organocatalysts in H2O/acetone (2:1) at room temperature. This method offers mild reaction conditions, excellent yields, easy workup, and readily accessible starting materials and catalysts. 相似文献
6.
The synthesis of 7,8‐dihydro‐5(6H)‐quinolinone ( 3 ) from commercially available 3‐amino‐2‐cyclohexen‐1‐one ( 1 ) and 3‐(dimethylamino)acrolein ( 4 ) in 23% yield avoids the preparation of propynal ( 2 ). Conversion of 5‐(4‐methylphenylsulfonyl)‐6,7,8,9‐tetrahydro‐5H‐pyrido[3,2‐b]azepine ( 12 ) to 6‐(4‐methylphenylsulfonyl)‐1,4,5,6‐tetrahydropyrazolo[3,4‐d]pyrido[3,2‐b]azepine ( 24 ) is described. Removal of the N‐(4‐methylphenylsulfonyl) group with 40% sulfuric acid in acetic acid gave the tricyclic azepine 26. Application of a similar series of reactions to 5‐(4‐nitrobenzoyl)‐6,7,8,9‐tetrahydro‐5H‐pyrido[3,2‐b]‐azepine ( 13 ) afforded 6‐(4‐nitrobenzoyl)‐1,4,5,6‐tetrahydropyrazolo[3,4‐d]pyrido[3,2‐b]azepine ( 25 ). 相似文献
7.
Heating of 1′‐(N‐substituted carbamoyl)methylspiro[2H‐1‐benzopyran‐2,2′‐[2H]indoles] with potassium hydroxide in ethanol yields diastereomeric 5a,13‐methano‐6H‐1,3‐benzoxazepino[3,2‐a]indole‐12‐carbox‐amides. Reduction of the latter with sodium borohydride affords 1,2,3,9a‐tetrahydro‐2‐hydroxyaryl‐9H‐pyrrolo[ 1,2‐a] indole‐3 ‐carboxamides. 相似文献
8.
《Journal of heterocyclic chemistry》2018,55(1):91-96
Reaction of 5,6‐dihydro‐4H‐pyrrolo[3,2,1‐ij]quinoline‐1,2‐dione ( 1 ) with two equivalents of some 6‐aminouracils (or 6‐amino‐2‐thiouracil) generates spirocyclic tetrahydrobenzo[if]quinolizines ( 7 ). The one‐pot, three‐component reaction of amido ketone ( 1 ) with 6‐aminouracil (or 6‐amino‐2‐thiouracil) and a cyclic six‐membered 1,3‐diketone produces spirocyclic tetrahydropyrrolo[3,2,1‐ij]quinolinones ( 15 ). 相似文献
9.
Federico Da Settimo Anna Maria Marini Gianluca Pardi Giampaolo Primofiore Silvia Salerno Francesca Simorini 《Journal of heterocyclic chemistry》2001,38(3):607-612
A new synthetic route to build the [1,2,4]triazino[3,4‐ f]purine nucleus is described. The novel [1,2,4]‐triazino[3,4‐ f]purine‐4,6,8(l H,7 H,9 H)‐trione derivatives were obtained by condensation of 8‐hydrazinotheophylline with appropriate glyoxylic acids via the intermediate hydrazones. 相似文献
10.
Khosrow Jadidi Ramin Ghahremanzadeh Peiman Mirzaei Ayoob Bazgir 《Journal of heterocyclic chemistry》2011,48(5):1014-1018
A one‐pot, three‐component method for the efficient and simple synthesis of novel 2′‐amino‐8′,9′‐dihydro‐3′H‐spiro[indoline‐3,5′‐pyrimido[4,5‐b]quinoline]‐2,4′,6′(7′H,10′H)‐trione derivatives in aqueous media is reported. J. Heterocyclic Chem., (2011). 相似文献
11.
This paper presents the synthesis of a series of 5,6‐dihydro‐4H,8H‐pyrimido[1,2,3‐cd]purine‐8,10(9H)‐dione ring system derivatives with a [1,2,3]triazole ring bonded in position 2. The procedure is based on cycloaddition of substituted alkyl azides to the terminal triple bond of 5,6‐dihydro‐2‐ethynyl‐9‐methyl‐4H,8H‐pyrimido[1,2,3‐cd]purine‐8,10(9H)‐dione ( 4 ). This cycloaddition produced two regioisomers ?5,6‐dihydro‐9‐methyl‐2‐(1‐substituted‐1H‐[1,2,3]triazol‐5‐yl)‐4H,8H‐pyrimido[1,2,3‐cd]purine‐8,10(9H)‐dione ( 7 ) and 2‐(1‐substituted‐1H‐[1,2,3]triazol‐4‐yl) derivative 8 . The required 2‐ethynyl deriva tive 4 was obtained from the starting 2‐unsubstituted compound 1 by bromination to yield the 2‐bromo derivative 2 , which was converted by Sonogashira reaction to trimethylsilylethyne 3 and finally, the protective trimethylsilyl group was removed by hydrolysis. 相似文献
12.
New Synthesis of Diazepino[3,2,1‐ij]quinoline and Pyrido[1,2,3‐de]quinoxalines via Addition–Elimination Followed by Cycloacylation
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Pier Giovanni Baraldi Emanuela Ruggiero Mojgan Aghazadeh Tabrizi 《Journal of heterocyclic chemistry》2014,51(1):101-105
This paper describes a convenient and efficient synthesis of new fused tricyclic diazepino[3,2,1‐ij]quinolines and substituted pyrido[1,2,3‐de]quinoxalines. o‐Phenylenediamines are transformed in the tricycle nucleus in only a few‐step synthetic sequence to produce ethyl 2,8‐dioxo‐1,2,3,4‐tetrahydro‐8H [1,4]diazepino[3,2,1‐ij]quinoline‐7‐carboxylate, ethyl 8‐oxo‐1,2,3,4‐tetrahydro‐8H‐[1,4]diazepino[3,2,1‐ij]quinoline‐7‐carboxylate and ethyl 2,7‐dioxo‐2,3‐dihydro‐1H,7H‐pyrido[1,2,3‐de]quinoxaline‐6‐carboxylate. The method is economical and simple to perform. 相似文献
13.
Mehdi M. Baradarani Bahman Ebrahimi Saatluo Shiva Ghabeli Zahra Shokri Masoumeh Shahbazi John A. Joule 《Journal of heterocyclic chemistry》2019,56(7):1999-2007
The tricyclic isatin, 5,6‐dihydro‐4H‐pyrrolo[3,2,1‐ij]quinoline‐1,2‐dione, undergoes three‐component, one‐pot reactions with 1‐aryl‐3‐methylpyrazole‐5‐amines and cyclohexane‐1,3‐diones producing hexacyclic spiro products, hexahydrospiro[pyrazolo[3,4‐b]quinoline‐4,1‐pyrrolo[3,2,1‐ij]quinoline‐2′,5(1H,4′H)‐diones]. Comparable spiro condensation products are also obtained using 4‐hydroxy‐2H‐1‐benzopyran‐2‐one in place of cyclohexane‐1,3‐diones. 相似文献
14.
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
15.
Antonio Da Settimo Anna Maria Marini Giampaolo Primofiore Federico Da Settimo Silvia Salerno Concettina La Motta Gianluca Pardi Pier Luigi Ferrarini Claudio Mori 《Journal of heterocyclic chemistry》2000,37(2):379-382
The synthesis of the title compounds 5H, 11H‐pyrido[2′,3′:2,3]thiopyrano[4,3‐b]indoles was accomplished by the Fischer indole cyclization of some 2,3‐dihydrothiopyrano[2,3‐b]pyridin‐4(4H)‐one phenylhydrazones and 7‐methyl‐2,3‐dihydrothiopyrano[2,3‐b]pyridin‐4(4H)‐one phenylhydrazones. The synthesis of the new 2,3‐dihydrothiopyrano[2,3‐b]pyridin‐4(4H)‐one, which was used as one of the starting compounds, is also described. 相似文献
16.
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
17.
《Journal of heterocyclic chemistry》2017,54(2):1199-1209
By reaction with sodium ethoxide and as a function of their structures, 2‐[(1‐alkyl(aryl)‐4‐cyano‐6,7‐dihydro‐5H‐cyclopenta[c ]pyridin‐3‐yl)oxy]acetamides 11 gave 1‐amino‐5‐alkyl(aryl)‐7,8‐dihydro‐6H‐cyclopenta[d ]furo[2,3‐b ]pyridine‐2‐carboxamides 10 and/or 1‐alkyl(aryl)‐3‐amino‐6,7‐dihydro‐5H‐cyclopenta[c ]pyridine‐4‐carbonitriles 12 . 相似文献
18.
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
19.
Diastereoselective Synthesis of (Z)‐6‐(2‐Oxo‐1,2‐dihydro‐3H‐indol‐3‐ylidene)‐3,3a,9,9a‐tetrahydroimidazo[4,5‐e]thiazolo[3,2‐b]‐1,2,4‐triazin‐2,7(1H,6H)‐diones
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Galina A. Gazieva Ekaterina A. Shishkova Ludmila B. Kulikova Natal'ya G. Kolotyrkina Natal'ya V. Sigay Angelina N. Kravchenko 《Journal of heterocyclic chemistry》2014,51(4):921-926
Two efficient and diastereoselective procedures for the synthesis of (Z)‐6‐(2‐oxo‐1,2‐dihydro‐3H‐indol‐3‐ylidene)‐3,3a,9,9a‐tetrahydroimidazo[4,5‐e]thiazolo[3,2‐b]‐1,2,4‐triazin‐2,7(1H,6H)‐diones by aldol‐crotonic condensation of 1,3‐dimethyl‐3a,9a‐diphenyl‐3,3a,9,9a‐tetrahydroimidazo[4,5‐e]thiazolo[3,2‐b]‐1,2,4‐triazin‐2,7(1H,6H)‐dione with isatins under acidic or basic catalysis are reported. Isomerization in (Z)‐7‐(1‐allyl‐2‐oxo‐1,2‐dihydro‐3H‐indol‐3‐ylidene)‐1,3‐dimethyl‐3a,9a‐diphenyl‐1,3a,4,9a‐tetrahydroimidazo[4,5‐e]thiazolo[2,3‐c]‐1,2,4‐triazin‐2,8(3H,7H)‐dione was observed under basic conditions. 相似文献
20.
Taisei Ueda Wataru Doi Shin‐Ichi Nagai Jinsaku Sakakibara 《Journal of heterocyclic chemistry》2000,37(5):1269-1272
Novel heterocycles [1,2,5]selenadiazolo[3,4‐e][1,4]diazepines 3a‐c , [1,2,5]thiadiazolo[3,4‐e]‐[1,4]diazepines 7a‐c , [1,2,5]selenadiazolo[3,4‐e][1,4]oxaepines 4a,b , [1,2,5]thiadiazolo[3,4‐e]‐[1,4]oxazepines 9a‐c and [1,2,5]selena(or thia)diazolo[3,4‐c][1,2,6]thiadiazines 10a,b were synthesized starting form 4,6‐dimethyl[1,2,5]se]enadiazolo[3,4‐d]pyrimidine‐5,7(4H,6H)‐dione 1 or 4,6‐dimethyl‐[1,2,5]thiadiazolo[3,4‐d]pyrimidine‐5,7(4H,6H)‐dione 5 . 相似文献