共查询到20条相似文献,搜索用时 656 毫秒
1.
《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
2.
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
3.
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
4.
New Synthesis of Diazepino[3,2,1‐ij]quinoline and Pyrido[1,2,3‐de]quinoxalines via Addition–Elimination Followed by Cycloacylation
下载免费PDF全文
![点击此处可从《Journal of heterocyclic chemistry》网站下载免费的PDF全文](/ch/ext_images/free.gif)
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
5.
Stephen P. Stanforth 《Journal of heterocyclic chemistry》2005,42(4):723-725
The 2,3‐dihydro‐7‐methyl‐1H,5H‐pyrido[3,2,1‐ij]quinoline‐1,5‐dione derivatives 9 and 10 were prepared from 3‐(5,7‐dimethoxy‐4‐methyl‐2‐oxo‐2H‐quinolin‐1‐yl)propionitrile ( 6 ). Cyclodehydration of the amide 8 gave 1,2‐dihydro‐7,9‐dimethoxy‐6‐methylpyimido[1,2‐a]quinolin‐3‐one ( 11 ). 相似文献
6.
7.
A. Shafiee J. Shahbazi Mojarrad M. A. Jalili H. R. Adhami F. Hadizadeh 《Journal of heterocyclic chemistry》2002,39(2):367-373
Starting from readily available p‐substituted‐benzylamines a series of ethyl 2‐alkylthio‐1‐substituted‐ben‐zylpyrrolo[2,3‐d]imidazole‐5‐carboxylates was prepared. In addition, starting from 2‐alkyl‐4(or 5)‐formylimidazoles and methyl 4′‐bromomethylbiphenyl‐2‐carboxylate a series of methyl substituted‐pyrrolo[2,3‐d]imidazole‐5‐carboxylates and methyl substituted‐pyrrolo[3,2‐d]imidazole‐5‐carboxylates was prepared. 相似文献
8.
Synthesis of the title compounds was achieved using the anils 2a , 2b , 2c , 2d , 2e and 5a , 5b , 5c derived from the 4‐aminopyrazole 1 as starting materials. These compounds were allowed to react with mercaptoacetic acid in boiling dry benzene to afford the corresponding thiazolidinones and spiro‐thiazolidinones 3a , 3b , 3c , 3d , 3e and 6a , 6b , 6c , respectively. Pictet—Spengler reaction of the 4‐aminopyrazole hydrochloride 7 with aromatic aldehydes and cyclic ketones resulted in the formation of new pyrazolo[4,3‐e]pyrrolo[1,2‐a]pyrazines 8a , 8b , 8c , 8d , 8e and 9a , 9b , respectively. Other derivatives of pyrazolo pyrrolopyrazines 10 and 11 were obtained via the reaction of the amino derivative 1 with 1,1′‐carbonyldiimidazol and CS2, respectively. J. Heterocyclic Chem., (2011). 相似文献
9.
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
10.
The three‐component reaction of N‐phenacylbenzothiazolium bromides, aromatic aldehydes and indane‐1,3‐dione in ethanol at room temperature in the presence of triethylamine as base afforded functionalized spiro[benzo[d]pyrrolo[2,1‐b]thiazole‐3,2′‐indenes] in good yields and with high diastereoselectivity. The 1H NMR data and single crystal structure clearly indicated that the obtained spiro compounds predominately have one diastereoisomer. 相似文献
11.
Carlos M. Martínez‐Viturro Domingo Domínguez 《Journal of heterocyclic chemistry》2007,44(5):1035-1043
12.
13.
2,3‐Dihydro‐1,3,4‐thiadiazoles, pyrazoles, pyrazolo[3,4‐d]pyridazines, thieno[2,3‐b]pyridines, pyrim‐idino[4′,5′:4,5]thieno[2,3‐b]pyridines and pyrrolo[3,4‐d]pyrazoles were obtained in a good yields by treatment of hydrazonoyl halides with each of alkyl carbodithioates, 3‐(dimethylamino)‐1‐naphtho[1,2‐d]furan‐2‐ylprop‐2‐en‐1‐one and N‐arylmalemides. 相似文献
14.
Mazaahir Kidwai Kavita Singhal Shweta Rastogi 《Journal of heterocyclic chemistry》2006,43(5):1231-1236
15.
H. S. El‐Kashef A. M. Kamal El‐Dean A. A. Geies J. C. Lancelot P. Dallemagne S. Rault 《Journal of heterocyclic chemistry》2000,37(6):1521-1526
The synthesis of the title compounds was achieved using the key intermediate ethyl 4,6‐dimethyl‐3‐(pyrrol‐1‐yl)thieno[2,3‐b]pyridine‐2‐ carboxylate 2. This latter compound was obtained via the interaction of the thienopyridine amino ester 1 with 2,5 dimethoxytetrahydrofuran in acidic medium. 相似文献
16.
Wolfgang Stadlbauer Hoai Van Dang Bernd Knobloch 《Journal of heterocyclic chemistry》2011,48(5):1039-1049
Pyrido[3,2,1‐jk]carbazoles 1 , synthesized from carbazoles and alkyl‐ or arylmalonates, gave regioselective electrophilic substitution reactions at position 5 such as chlorination to 5‐chloro derivatives 2 , nitration to 5‐nitro compounds 3 , or hydroxylation to 5‐hydroxy derivatives 4 . 5‐Hydroxy compounds 4 gave on treatment with strong bases ring contraction to 5 , 6 or the ring opening product 7 . Exchange of the chloro group in 2 with azide or amines gave the corresponding azides 8 and the 5‐amino derivatives 9 and 10 . Alkylation of 1 with benzyl chloride or allyl bromide resulted in the formation of 5‐C‐alkylated products 11 together with 4‐alkyloxy derivatives 12 . J. Heterocyclic Chem., 48, 1039 (2011). 相似文献
17.
Raghunath B. Toche Bhausaheb K. Ghotekar Dhananjay B. Kendre Muddassar A. Kazi Madhukar N. Jachak 《Journal of heterocyclic chemistry》2008,45(6):1711-1717
18.
Shogo Ihara Takashi Soma Daigo Yano Shunichi Aikawa Yasuhiko Yoshida 《Journal of heterocyclic chemistry》2011,48(3):577-581
The cycloaddition reaction of cyclic imidates, 2‐benzyl‐5,6‐dihydro‐4H‐1,3‐oxazines 1a , 1b , 1c , 1d , 1e , 1f , with dimethyl acetylenedicarboxylate 2 , trimethyl ethylenetricarboxylate 4 , or dimethyl 2‐(methoxymethylene)malonate 6 afforded new fused heterocyclic compounds, such as methyl (6‐oxo‐3,4‐dihydro‐2H‐pyrrolo[2,1‐b]‐1,3‐oxazin‐7‐ylidene)acetates 3a , 3b , 3c , 3d , 3e , 3f (71–79%), dimethyl 2‐(6‐oxo‐3,4,6,7‐tetrahydro‐2H‐pyrrolo[2,1‐b]‐1,3‐oxazin‐7‐yl)malonates 5b , 5c , 5d , 5e , 5f (43–71%), or methyl 6‐oxo‐3,4‐dihydro‐2H,6H‐pyrido[2,1‐b]‐1,3‐oxazine‐7‐carboxylates 7a , 7b , 7c , 7d , 7e , 7f (32–59%), respectively. In these reactions, 1a , 1b , 1c , 1d , 1e , 1f (cyclic imidates, iminoethers) functioned as their N,C‐tautomers (enaminoethers) 2 to α,β‐unsaturated esters 2 , 4, and 6 to give annulation products 3 , 5 , and 7 following to the elimination of methanol, respectively. J. Heterocyclic Chem., (2011). 相似文献
19.
Emma E. O'Dwyer Nessa S. Mullane Timothy P. Smyth 《Journal of heterocyclic chemistry》2011,48(2):286-294
A modular synthesis of selectively‐substituted pyrrolo[2,1‐b]thiazoles (Δ6 isomeric form) has been implemented, involving a distinctive bicyclization reaction of a mucobromic acid derivative followed by a Suzuki‐Miyaura coupling. A novel process of Δ6 to Δ7 isomerization of the pyrrolothiazole structure was uncovered that appears to involve a 1,4‐addition‐1,2‐elimination mechanism. Preparation of 1,5‐dihydropyrrol‐2‐one structures, selectively substituted at the 3‐ and 4‐positions, was also achieved using the mucobromic acid synthon in a reductive amination process. J. Heterocyclic Chem., (2011). 相似文献
20.
Three previously undescribed dihydrofolate reductase (DHFR) inhibitors, Nα‐[4‐[N‐[(2,4‐diaminopyrrolo[2,3‐d]pyrimidin‐5‐yl)methyl]amino]benzoyl]‐Nδ‐hemiphthaloyl‐L‐ornithine (7) , Nα‐ [4‐ [N‐[(2,4‐diaminothieno[2,3‐d]pyrimidin‐5‐yl)methyl]amino]benzoyl]‐ Nδ‐hemiphthaloyl‐L‐ornithine (8) , and N‐[4‐[N‐[(2,4‐diaminothieno[2,3‐d]pyrimidin‐5‐yl)methyl]amino]benzoyl]‐L‐glutamic acid (12) , were synthesized and their antifolate activity was assessed. The ability of 7 and 8 to bind to DHFR and inhibit the growth of CCRF‐CEM human lymphoblastic leukemia cells in culture were dramatically reduced in comparison with the corresponding pteridine analogue, Nα‐(4‐amino‐4‐deoxypteroyl)‐Nδ‐hemiphmaloyl‐L‐ornithine ( 1 , PT523). In a similar manner, the antifolate activity of 12 was markedly reduced in comparison with that of the corresponding glutamate analogue, aminopterin ( 5 , AMT). In contrast, 7, 8 , and 12 all displayed excellent affinity for the reduced folate carrier (RFC) of CCRF‐CEM cells as measured by a standard competitive influx assay. Lack of a consistent correlation between the results of the growth inhibition assays and those of the DHFR and RFC binding assays results suggest that additional factors also play a role in the antifolate activity of these compounds. 相似文献