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1.
Hamdi M. Hassaneen Tayseer A. Abdallah Hyam A. Abdelhadi Huwaida M. E. Hassaneen Richard M. Pagni 《Heteroatom Chemistry》2003,14(6):491-497
2‐Dimethylaminomethylene‐ and 2‐ethoxymethylene‐1,3‐indendione 1a,b react with 6‐amino‐2‐thioxopyrimidin‐4(3H)‐one 2 in boiling acetic acid to give 2‐thioxo‐1,3‐dihydroindeno[3,2‐d]pyrimidino[4,5‐b]pyridine‐4,9‐dione ( 4 ). The latter compound reacts with hydrazonoyl chlorides 5a–c to afford products 12a–c . Formamidine 15 reacts with indene‐1,3‐dione in boiling ethanol to give acyclic compound 16 , which cyclizes to 12a in boiling glacial acetic acid. Also, enaminone 1a reacts with heterocyclic amines 17a–e in boiling ethanol, affording the corresponding substitution products 18a–c , respectively. The latter products 18a–c cyclize in glacial acetic acid to give 19a–c , respectively. The structures of the newly synthesized compounds are established on the basis of chemical and spectroscopic evidence. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:491–497, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10166 相似文献
2.
The benzo[a]heptalene formation from 4‐[(R‐sulfonyl)acetyl]heptalene‐5‐carboxylates 15 and 5‐[(R‐sulfonyl)acetyl]heptalene‐4‐carboxylates 16 (R=Ph or morpholino) in the presence of R′SO2CH2Li and BuLi has been investigated (Scheme 6). Only the sulfonyl moiety linked to the C?O group at C(4) of the heptalene skeleton is found at C(3) of the formed benzo[a]heptalene‐2,4‐diols 3 in accordance with the general mechanism of their formation (Scheme 3). Intermediates that might rearrange to corresponding 2‐sulfonylbenzo[a]heptalene‐1,3‐diols lose HO? under the reaction conditions to yield the corresponding cyclopenta[d]heptalenones of type 11 (Schemes 6 and 7). However, the presence of an additional Me group at C(α) of the lithioalkyl sulfones suppresses the loss of HO?, and 4‐methyl‐2‐sulfonylbenzo[a]heptalene‐1,3‐diols of type 4c have been isolated and characterized for the first time (Schemes 8 and 10). A number of X‐ray crystal‐structure analyses of starting materials and of the new benzo[a]heptalenes have been performed. Finally, benzo[a]heptalene 4c has been transformed into its 1,2,3‐trimethoxy derivative 23 , a benzo[a]heptalene with the colchicinoid substitution pattern at ring A (Scheme 11). 相似文献
3.
Xuerui Wang Wenxue Zhang Hongjuan Shen Wei Zhang 《Journal of heterocyclic chemistry》2013,50(3):501-505
A one‐pot synthesis of pyrrolo[1,2‐a]quinolin‐1‐ones has been developed from the reactions of 5‐hydroxy‐1‐arylpyrrolidin‐2‐ones with 1,3‐dicarbonyl compounds under the promotion of H3PO4/P2O5 or HOAc/H2SO4. The pyrrolo[1,2‐a]quinolin‐1‐ones are formed by two‐step reactions, that is, the coupling of N‐acyliminium ion intermediates produced from 5‐hydroxy‐1‐arylpyrrolidin‐2‐ones with 1,3‐dicarbonyls and subsequent Friedel–Crafts reactions of the resulting ketone with the aryl ring. 相似文献
4.
Synthesis of 2,5,7‐Triaryl‐4,7(6,7)‐dihydropyrazolo[1,5‐a]pyrimidine‐3‐carbonitriles by Reaction of 5(3)‐Amino‐3(5)‐aryl‐1H‐pyrazole‐4‐carbonitriles with Chalcones
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Maksim A. Kolosov Dmitriy A. Beloborodov Olesia G. Kulyk Valeriy D. Orlov 《Journal of heterocyclic chemistry》2014,51(Z1):E89-E92
The reaction of 5(3)‐amino‐3(5)‐aryl‐1H‐pyrazole‐4‐carbonitriles with 1,3‐diaryl‐2‐propen‐1‐ones (chalcones) in refluxing DMF leads to 2,5,7‐triaryl‐4,7(6,7)‐dihydropyrazolo[1,5‐a]pyrimidine‐3‐carbonitriles. In DMSO solution, the latter exist in equilibrium of two tautomeric 4,7‐dihydropyrazolo[1,5‐a]pyrimidines and 6,7‐dihydropyrazolo[1,5‐a]pyrimidines in various ratios, depending on the nature of aryl substituents in chalcone building blocks. 相似文献
5.
N‐benzimidazol‐2‐yl imidate type 1 reacts with thiourea, carbon disulfide, cyanamide, and hydrazide to give, respectively, [1,2‐a] benzimidazolo‐1,3,5‐triazin‐2‐thione 2 , [1,2‐a] benzimidazolo‐1,3,5‐thiadiazin‐2‐thione 3 , [1,2‐a] benzimidazolo‐1,3,5‐triazin‐2‐amine 4 , and [1,2‐a] benzimidazol‐2‐yl amidrazone 5 with good yields. Structures elucidation of all newly synthesized heterocyclic compounds was based on the data of IR, 1H NMR, 13C NMR, elemental analysis, and MS of some products. © 2010 Wiley Periodicals, Inc. Heteroatom Chem 21:279–283, 2010; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20618 相似文献
6.
Nadia A. Abdel‐Riheem Nora M. Rateb Ali A. Al‐Atoom Abdou O. Abdelhamid 《Heteroatom Chemistry》2003,14(5):421-426
1,2,4‐Triazolo[4,3‐a]pyrimidines, thiadiazolines, selenadiazolines, and unsymmetrical azines were synthesized via reactions of a 4‐isopropylbenzoyl bromide 4‐nitrophenylhydrazone with each of potassium thiocyanate, potassium selenocyanate, ethyl 6‐methyl‐4‐[4‐(methylethyl)phenyl]‐2‐methylthio‐3,4‐dihydropyrimidine‐5‐carboxylate, and alkyl carbodithioate. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:421–426, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10156 相似文献
7.
The reaction of N‐phenylimidoyl isoselenocyanates 1 with 2‐amino‐1,3‐thiazoles 10 in acetone proceeded smoothly at room temperature to give 4H‐1,3‐thiazolo[3,2‐a] [1,3,5]triazine‐4‐selones 13 in fair yields (Scheme 2). Under the same conditions, 1 and 2‐amino‐3‐methylpyridine ( 11 ) underwent an addition reaction, followed by a spontaneous oxidation, to yield the 3H‐4λ4‐[1,2,4]selenadiazolo[1′,5′:1,5] [1,2,4]selenadiazolo[2,3‐a]pyridine 14 (Scheme 3). The structure of 14 was established by X‐ray crystallography (Fig. 1). Finally, the reaction of 1‐methyl‐1H‐imidazole ( 12 ) and 1 led to 3‐methyl‐1‐(N‐phenylbenzimidoyl)‐1H‐imidazolium selenocyanates 15 (Scheme 4). In all three cases, an initially formed selenourea derivative is proposed as an intermediate. 相似文献
8.
Gyrgy Keglevich Helga Szelke gnes Blint Tímea Imre Krisztina Ludnyi Zoltn Nagy Mikls Hanusz Klmn Simon Veronika Harmat Lszl Tke 《Heteroatom Chemistry》2003,14(5):443-451
A series of new P‐methylphenyl P‐heterocycles are introduced. The para and ortho substituted 2,5‐dihydro‐1H‐phosphole oxides ( 1a and 1b ) were converted to the double‐bond isomers ( A and B ) of 1,2‐dihydrophosphinine oxides ( 3a and 3b ) via the corresponding phosphabicyclo[3.1.0]hexane oxides ( 2a or 2b ). Isomeric mixture ( A and B ) of the dihydrophosphinine oxides ( 3a and 3b ) gave, in turn, the isomers ( A and B ) of phosphabicyclo[2.2.2]oct‐5‐enes ( 4a and 4b ) or a phosphabicyclo[2.2.2]octa‐5,7‐diene ( 5 ) in Diels‐Alder reaction with dienophiles. The bridged P‐heterocycles ( 4 and 5 ) were useful in the photo‐ or thermoinduced fragmentation‐related phosphinylation of hydroxy compounds and amines. The new precursors ( 4a and 4b ) were applied in mechanistic investigations. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:443–451, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10176 相似文献
9.
Yulin Ling Haochong Liu Aiting Zheng Guobin Li Xiaofang Li 《Journal of heterocyclic chemistry》2013,50(5):1009-1013
The reaction involving 4‐phenyl‐octahydro‐pyrano[2,3‐d]pyrimidine‐2‐thione, ethyl chloroacetate and the appropriate aromatic aldehyde yielded 2‐arylmethylidene‐5‐phenyl‐5a,7,8,9a‐tetrahydro‐5H,6H‐pyrano[2,3‐d][1,3]thiazolo[3,2‐a]pyrimidin‐3(2H)‐ones. The 1,3‐dipolar cycloaddition of 2‐arylmethylidene‐5‐phenyl‐5a,7,8,9a‐tetrahydro‐5H,6H‐pyrano[2,3‐d][1,3]thiazolo[3,2‐a]pyrimidin‐3(2H)‐ones with azomethine ylide generated by a decarboxylative route from sarcosine and acenaphthenequinone afforded 4′‐aryl‐1′‐methyl‐5″‐phenyl‐5a″,7″,8″,9a″‐tetrahydro‐2H,5″H,6″H‐dispiro[acenaphthylene‐1,2′‐pyrrolidine‐3′,2″‐pyrano[2,3‐d][1,3]thiazolo[3,2‐a]pyrimidine]‐2,3″‐diones in moderate yields. The structures of the products were determined and characterized thoroughly by NMR, MS, IR, elemental analysis, and X‐ray crystallographic analysis. 相似文献
10.
Alkylation of 2‐hydroxy‐4H‐pyrido[1,2‐a]pyrimidin‐4‐one ( 1 ) was investigated under solid–liquid phase transfer catalysis conditions (PTC), using tetrabutylammonium bromide and potassium carbonate. The reaction with alkyl halides led to the formation of various 2‐alkoxy products, in fair yields. Reaction of compound 1 with epichlorohydrin and chloroacetonitrile, under the same PTC conditions, afforded novel O1,O3‐disubstituted glycerol and oxazolopyridopyrimidone betaine derivatives, respectively. Some 3‐halo‐, 3,3‐dihalo, and/or 2,3‐dihalopyrido[1,2‐a]pyrimidines were also prepared using different halogenating agents at different reaction conditions. © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:19–27, 2007; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20245 相似文献
11.
Fatemeh Esmaeili‐Marandi Issa Yavari Mina Saeedi Mohammad Mahdavi Abbas Shafiee 《Helvetica chimica acta》2016,99(3):187-190
Novel derivatives of pyrazino[2,1‐a]isoindolediones were synthesized through 6‐exo‐dig intramolecular hydroamination of 2,3‐dihydro‐3‐oxo‐2‐(prop‐2‐yn‐1‐yl)‐1H‐isoindole‐1‐carboxamides followed by 1,3‐H shift, in the presence of sodium hydride in DMF at 80°. All products were obtained in good yields (60 – 80%) within short reaction time (40 – 60 min). 相似文献
12.
Regina Janciene Zita Stumbreviciute Ausra Vektariene Lidija Kosychova Romualdas Sirutkaitis Algirdas Palaima Zita Staniulyte Benedikta D. Puodziunaite 《Heteroatom Chemistry》2008,19(1):72-81
A number of 1‐substituted 4H,5H,6H‐[1,3]thiazolo[3,2‐a][1,5]benzodiazepinium‐11‐bromides and S‐(2‐oxo‐2‐phenyl‐X‐(p)‐ethyl)‐3‐(2‐methyl‐1H‐benzimidazol‐1‐yl) propane (or butane) thioate hydrobromides were obtained by direct reaction of the 5‐acetyl(or formyl, or anilinocarbonyl)‐substituted tetrahydro‐1,5‐benzodiazepine‐2‐thiones with aromatic α‐bromoketones. 2‐[(1‐Acetyl‐2(or 3)‐methyl‐2,3‐dihydro‐1H‐1,5‐benzodiazepin‐4‐yl) sulfanyl]‐1‐phenylethanones as intermediates of the formation of thiazolo [3,2‐a][1,5]benzodiazepine and N‐substituted 2‐methyl‐1H‐benzimidazole derivatives have been synthesized. Semiempirical AM1 calculations of a mechanism and energetic parameters for the heptatomic nucleus rearrangement to benzimidazole ring are presented. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:72–81, 2008; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20414 相似文献
13.
Essam Kh. Ahmed 《Heteroatom Chemistry》2003,14(3):201-207
Convenient syntheses of 3‐substituted ethyl 4‐oxo‐2‐thioxo‐1,2,3,4,5,6,7,8‐octahydropyrid[4′,3′:4,5]thieno[2,3‐d]pyrimidine‐7‐carboxylates 3a, b, 6, 11–13 , ethyl 3‐methyl‐5‐oxo‐2,3,6,9‐tetrahydro‐5 H‐pyrido[4′,3′:4,5]thieno[2,3‐d][1,3]thiazolo[3,2‐a]pyrimidine‐8‐7H‐carboxylate ( 4 ), and ethyl 2‐methyl‐5‐oxo‐2,3,6,9‐tetrahydro‐5H‐pyrido[4′,3′:4,5]thieno[2, 3‐d][1,3]thiazolo[3,2‐a]pyrimidine‐8[7H]carboxylate ( 8 ) from diethyl 2‐isothiocyanato‐4,5,6,7‐tetrahythieno[2,3‐c]pyridine‐3,6‐dicarboxylate ( 1 ) are reported. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:201–207, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10131 相似文献
14.
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
15.
Ahmed S. A. Youssef Kamal A. Kandeel Fouli A. Fouli Wael S. I. Abou‐Elmagd 《Heteroatom Chemistry》2005,16(1):6-11
2‐Amino‐3‐cyano‐4,5,6,7‐tetrahydrobenzo[b]thiophene 1a or 2‐amino‐3‐cyano‐4,7‐di‐ phenyl‐5‐methyl‐4H‐pyrano[2,3‐c]pyrazole 2a reacted with phenylisocyanate in dry pyridine to give 2‐(3‐phenylureido)‐3‐cyanobenzo[b]thiophene 1b or 2‐disubstituted amino‐3‐cyanopyranopyrazole 2b derivative. However, when 1a and 2a were refluxed with carbon disulfide in 10% ethanolic sodium hydroxide solution, they afforded the thieno[2,3‐d]pyrimidin‐2,4‐dithione derivative 5 in the former case, 2,4‐dicyano‐1,3‐bis(dithio carboxamino)cyclobuta‐1,3‐ diene 6 and pyrazolopyranopyrido[2,3‐d]pyrimidin‐ 2,4‐dithione derivative 7 in the latter one. Treatment of 2a with thiourea in refluxing ethanol in the presence of potassium carbonate gave 2,2′‐dithiobispyrimidine derivative 9 (major) in addition to pyranopyrazole derivative 10 and 2,2′‐dithiobis ethoxypyrimidine derivative 11 in minor amounts. The structures of all products were evidenced by microanalytical and spectral data. © 2005 Wiley Periodicals, Inc. Heteroatom Chem 16:6–11, 2005; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20070 相似文献
16.
17.
A new example of [2+4] cycloaddition of the low‐coordinated diphospha‐analog of butadiene protected with a 2,4‐di‐tert‐butyl‐6‐methylphenyl group has been described. X‐ray structure investigations of monomer 4b and dimer 5a have been reported for the first time. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:231–234, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10123 相似文献
18.
Abolghasem Davoodnia Mohammad Rahimizadeh Hoda Atapour‐Mashhad Niloofar Tavakoli‐Hoseini 《Heteroatom Chemistry》2009,20(6):346-349
The reaction of 2‐amino‐4,5‐dimethyl‐ thiophene‐3‐carboxamide with iso(and isothio) cyanates for the synthesis of thieno[2,3‐d]pyrimidines has been investigated. The reactions under microwave irradiation in the presence of N,N‐dimethyl acetamide as solvent gave 5,6‐dimethylthieno[2,3‐d]pyrimidine‐2,4(1H,3H)‐dione, 5,6‐dimethyl‐2‐thioxo‐2,3‐dihy‐ drothieno[2,3‐d]pyrimidin‐4(1H)‐one, and 2‐aryla‐ mino‐5,6‐dimethylthieno[2,3‐d]pyrimidin‐4(3H)‐one derivatives. These reactions probably proceed through intermediates 4,5‐dimethyl‐2‐substitutedcarbamoth‐ ioylaminothiophene‐3‐carboxamides. Two of these intermediates were isolated. © 2009 Wiley Periodicals, Inc. Heteroatom Chem 20:346–349, 2009; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20557 相似文献
19.
A. A. F. Wasfy 《Heteroatom Chemistry》2003,14(7):576-580
4‐Allylthio‐2‐arylquinazolines 4a–c undergo cyclization by action of bromine to furnish 5‐aryl‐3‐bromomethyl‐2,3‐dihydrothiazolo[3,2‐c]quinazolin‐4‐ium bromides 5a–c . Compounds 5a–c undergo ring opening by action of water under acid catalysis to afford the corresponding dibromide derivatives 6a–c . Bromination of 3‐allyl‐2‐aryl‐4(3H)quinazolinethiones 7a–c leads to 5‐aryl‐2‐bromomethyl‐2,3‐dihydrothiazolo[3,2‐c]quinazolin‐4‐ium bromides 8a–c . However, anhydro‐3‐hydroxy‐5‐aryl‐1,3‐thiazolo[3,2‐c]quinazolin‐4‐ium hydroxide 10a–c were prepared by the cyclodehydration of the corresponding thioglycolic acids 9a–c with Ac2O. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:576–580, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10148 相似文献
20.
Yu‐Xin Li You‐Ming Wang Xiao‐Ping Yang Su‐Hua Wang Zheng‐Ming Li 《Heteroatom Chemistry》2003,14(4):342-344
A useful synthesis of 3‐methylthio‐6‐methyl‐pyrano[4,3‐c]pyrazol‐4(2H)‐ones via 3‐(bis‐methylthio)methylene‐5,6‐dihydro‐6‐alkyl(aryl)‐2H‐pyran‐2,4‐dione with hydrazine as well as methyl and phenyl hydrazines is described and the mechanism of the formation is discussed. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:342–344, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10158 相似文献