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Journal articles on the topic '4-oxopyrido[2,3-d]pyrimidines synthesis'

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Published: 4 June 2021

Last updated: 4 February 2022

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1

Borrell, José I., Jordi Teixidó, Blanca Martínez-Teipel, et al. "An Unequivocal Synthesis of 4-Amino-1,5,6,8-tetrahydropyrido[2,3-d]pyrimidine-2,7-diones and 2-Amino-3,5,6,8-tetrahydropyrido[2,3-d]pyrimidine-4,7-diones." Collection of Czechoslovak Chemical Communications 61, no. 6 (1996): 901–9. http://dx.doi.org/10.1135/cccc19960901.

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An unequivocal set of procedures for the synthesis of 4-amino-1,5,6,8-tetrahydropyrido[2,3-d]pyrimidine-2,7-diones (7) and 2-amino-3,5,6,8-tetrahydropyrido[2,3-d]pyrimidine-4,7-diones (8), in a maximum of four steps from an α,β-unsaturated ester 1, is reported. Thus, the acid hydrolysis of the 2,4-diaminopyrido[2,3-d]pyrimidines 3 yields the 4-amino-2-oxopyrido[2,3-d]pyrimidines 7 while the cyclization of the Michael adducts 9 (formed by reaction of 1 and methyl cyanoacetate) with guanidine affords the corresponding 2-amino-4-oxopyrido[2,3-d]pyrimidines 8. Both isomers were also obtained by hy

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2

Mohamed, Mosaad, Ramdan El-Domany, and Rania Abd El-Hameed. "Synthesis of certain pyrrole derivatives as antimicro-bial agents." Acta Pharmaceutica 59, no. 2 (2009): 145–58. http://dx.doi.org/10.2478/v10007-009-0016-9.

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Synthesis of certain pyrrole derivatives as antimicro-bial agentsIn an effort to establish new pyrroles and pyrrolo[2,3-d] pyrimidines with improved antimicrobial activity we report here the synthesis andin vitromicrobiological evaluation of a series of pyrrole derivatives. A series of new 2-aminopyrrole-3-carbonitriles (1a-d) were synthesized from the reaction of benzoin, primary aromatic amines and malononitrile, from which a number of pyrrole derivatives (2a-dto5a-d) and pyrrolo[2,3-d]pyrimidines (6a-dto10a, d) were synthesized. Thein vitroantimicrobial testing of the synthesized compounds

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3

Hossain, M. I., and M. M. H. Bhuiyan. "Synthesis and Antimicrobial Activities of Some New Thieno and Furopyrimidine Derivatives." Journal of Scientific Research 1, no. 2 (2009): 317–25. http://dx.doi.org/10.3329/jsr.v1i2.2299.

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Fused pyrimidines, 8,9-dimethyl[1,2,4]triazolo[4,3-c]thieno[3,2-e]pyrimidine 5, 3,8,9-trimethyl[1,2,4]triazolo[4,3-c]thieno[3,2-e]pyrimidine 6, 4-benzylidinehydrazono-5,6 dimethylthieno[2,3-d]pyrimidine 7, 4-[4/-hydroxybenzylidine]hydrazono-5,6-dimethylthi-eno[2,3-d]pyrimidine 8, 4-[4/-tolylidin]hydrazono-5,6-dimethylthieno[2,3-d]pyrimidine 9, 4-[4/-nitrobenzylidine]hydrazono-5-ethyl-6-methylthieno[2,3-d]pyrimidine 10 and 4-[4/-chlorobenzylidine]hydrazono-5-ethyl-6-methylthieno[2,3-d]pyrimidine 11 are prepared in good yield by an initial treatment of 2-amino-4,5-dimethylthiophene-3-carbonitril

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4

Azam, Mohammed Afzal, Loganathan Dharanya, Charu Chandrakant Mehta, and Sumit Sachdeva. "Synthesis and biological evaluation of some novel pyrazolopyrimidines incorporating a benzothiazole ring system." Acta Pharmaceutica 63, no. 1 (2013): 19–30. http://dx.doi.org/10.2478/acph-2013-0001.

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In the present study, a series of benzothiazol derivatives 3a-l containing pyrazolo[3,4-d]pyrimidine moiety at the second position were synthesized and characterized by analytical and spectral data. The compounds were tested for their in vitro antimicrobial activity. Compounds 1-(1,3-benzothiazol-2- yl)-3-methyl-4-phenyl-1H-pyrazolo[3,4-d]pyrimidine (3a), 1- (1,3-benzothiazol-2-yl)-4-(4-chlorophenyl)-3-methyl-1H-pyrazolo[ 3,4-d]pyrimidine (3d) and 1-(1,3-benzothiazol-2-yl)- 3-methyl-4-substituted phenyl-1H-pyrazolo[3,4-d]pyrimidines (3h-j) showed significant inhibitory activity against P. aeru

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5

Edrees, Mastoura M. "Synthesis of 4-hydrazinopyrazolo[3,4-d]pyrimidines and their Reactions with Carbonyl Compounds." Journal of Chemical Research 37, no. 1 (2013): 6–10. http://dx.doi.org/10.3184/174751912x13543818811749.

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Synthesis of a new 4-hydrazinopyrazolo[3,4- d]pyrimidine was achieved via heating (4,6-dithioxo-1 H-pyrazolo[3,4- d] pyrimidin-3-yl)acetonitrile with hydrazine hydrate. Reactions of the latter product with thiophene-2-carbaldehyde and ethyl hydrazonoacetoacetate analogues afforded the corresponding hydrazone and pyrazole derivatives, respectively. Similarly, condensation of 2-[6-(benzylsulfanyl)-4-hydrazino-1 H-pyrazolo[3,4- d]pyrimidin-3-yl]acetonitrile with thiophene-2-carbaldehyde and ethyl hydrazonoacetoacetate analogues gave the respective hydrazone and pyrazolone derivatives. Alkylation

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6

Ahmed, Essam Kh, Mohamed A. Ameen, and Fathy F. Abdel-Latif. "Microwave-Assisted Synthesis of Novel Imidazo- and Pyrimidopyrido[4’,3’:4,5]thieno[2,3-d]pyrimidines." Zeitschrift für Naturforschung B 60, no. 2 (2005): 221–26. http://dx.doi.org/10.1515/znb-2005-0216.

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It is reported on the microwave-assisted synthesis of imidazo- and pyrimidopyrido [4’,3’:4,5]thieno[ 2,3-d]pyrimidines from 2-ethoxymethylene-amino-3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]- pyridine-6-carboxylic acid ethyl ester and 4-chloro-pyridothieno[2,3-d]pyrimidine.

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7

Thokchom, Herojit S., Anita D. Nongmeikapam, and Warjeet S. Laitonjam. "Synthesis of fused pyrazolo-, isoxazolo-, pyrimido-, and pyridopyrimidines." Canadian Journal of Chemistry 83, no. 8 (2005): 1056–62. http://dx.doi.org/10.1139/v05-054.

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A systematic study of the synthesis of the 5,7-diaryl-4-oxo-pyrazolo[3,4-d]pyrimidin-6-thiones (3), 2-phenyl-5,7-bis(2′-methylphenyl)-4-oxo-pyrazolo[3,4-d]pyrimidin-6-thiones (4b), 2(3H)-3-phenyl-5,7-diaryl-4-oxo-pyrazolo[3,4-d]pyrimidin-6-thiones (5), 5,7-diaryl-4-oxo-isoxazolo[5,4-d]pyrimidin-6-thiones (7), 3,5,7-triaryl-2,3-dihydro-4-oxo-isoxazalo[5,4-d]pyrimidin-6-thiones (8), 2-amino-6,8-diaryl-5-oxo-pyrimido[4,5-d]pyrimidin-7-thiones (9), 3,4-dihydro-2-amino-4-phenyl-6,8-diaryl-5-oxo-pyrimido[4,5-d]pyrimidin-7-thiones (10), 3-cyano-6,8-diaryl-2,5-dioxo-pyrido[2,3-d]pyrimidin-7-thiones (1

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8

Salahuddin, Md, Sunil Kakad, and S. M. Shantakumar. "Synthesis of Some Novel Thieno[2, 3-d] pyrimidines and their Antibacterial Activity." E-Journal of Chemistry 6, no. 3 (2009): 801–8. http://dx.doi.org/10.1155/2009/361282.

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Bromination of intermediate 1-[4-(6, 7-dihydro-5H-cyclopenta [4, 5] thieno[2, 3-d]pyrimidin-4-yl amino) phenyl] ethanone(4)yielded(5). Which upon reaction with different substituted benzothiazoles give a novel series of pyrimidine[6(a-g)]. However reaction of(5)with 4-chloro-2-triflouro acetyl aniline provided(6h). Similarly reaction of(5)with 5-amino tetrazole & 2-amino benzimidazole produced(6i)&(6j)respectively. All the synthesized compounds were tested against bacteria (Gram positive and Gram negative).

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9

Youssif, Shaker, and Fatmah Agili. "One-pot Synthesis of Fused 2-Thiouracils: Pyrimidopyrimidines, Pyridopyrimidines and Imidazolopyrimidines." Zeitschrift für Naturforschung B 63, no. 7 (2008): 860–64. http://dx.doi.org/10.1515/znb-2008-0709.

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Several 6-substitued-1-methyl-2,5,7,8-tetrahydro-2-thiopyrimido[4,5-d]pyrimidine-4-ones and ethyl 7-amino-5-aryl-1-methyl-4-oxo-1,2,3,4-tetrahydro-2-thiopyrido[2,3-d]pyrimidines-6-carboxylates were synthesized by treatment of 6-amino-1-methyl-2-thiouracil with primary amines and formalin (40%), and with ethyl 3-aryl-2-cyanoacrylate respectively. 8-Substituted-7-hydroxy-3- methyl-2-thioxanthines were synthesized by the treatment of 6-amino-1-methyl-5-nitroso-2-thiouracil with benzylidene-anilines. Elemental and spectral analyses were performed for the new compounds.

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10

Otero, Iran, Holger Feist, Dirk Michalik, Manfred Michalik, José Quincoces та Klaus Peseke. "Synthesis of Iso-C-nucleoside Analogues from 1-(Methyl 2-O-benzyl-4,6- O-benzylidene-3-deoxy-α-D-altropyranosid-3-yl)but-3-yn-2-ones". Zeitschrift für Naturforschung B 60, № 11 (2005): 1175–85. http://dx.doi.org/10.1515/znb-2005-1110.

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1-(Methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-α-D-altropyranosid-3-yl)but-3-yn-2-one (3a) reacted with 3-amino-1H-1,2,4-triazole and 5-aminopyrazole-4-carboxylic acid derivatives in the presence of base to furnish the triazolo[1,5-a]pyrimidine (5) and the pyrazolo[1,5- a]pyrimidines (8a - d), respectively. Treatment of 1-(methyl 2-O-benzyl-4,6-O-benzylidene-3- deoxy-α-D-altropyranosid-3-yl)-4-phenyl-but-3-yn-2-one (3b) with cyanacetamide, 2-cyano-N- (4-methoxyphenyl)acetamide und N-aryl-3-oxo-butyramides afforded the substituted nicotinonitriles (11a - d). Furthermore, reaction of 3b with 2-b

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11

Hafez, Hend N., Abdel-Rhman B. A. El-Gazzar, and Magdi E. A. Zaki. "Simple approach to thieno[3,2-d]pyrimidines as new scaffolds of antimicrobial activities." Acta Pharmaceutica 66, no. 3 (2016): 331–51. http://dx.doi.org/10.1515/acph-2016-0029.

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Abstract 6ʹ-(4-Chlorophenyl)-spiro[cyclohexane-1,2ʹ-thieno[3,2-d][1,3] oxazin]-4ʹ(1ʹH)-one (1) was synthesized and used as a starting material for the synthesis of a novel series of spiro compounds having biologically active sulfonamide 2a-e and 3ʹ-(4-acetylphenyl)-6ʹ- (4-chlorophenyl)-1ʹH-spiro[cyclohexane-1,2ʹ-thieno[3,2-d] pyrimidine-4ʹ(3ʹH)-one (3). Compound 2a was used as a key intermediate for the synthesis of sulfonyl carbothioamide derivatives 4a-c. Also, compound 3 was used as an intermediate for the synthesis of 3ʹH-spiro[cyclohexane-1,2ʹ-thieno[3,2-d]pyrimidin]-3ʹ-yl] phenyl}-2-imin

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12

Marchalín, Štefan, Františka Pavlíková, and Dušan Ilavský. "Synthesis and spectral properties of pyrrolo[3',4':5,6]-4H-pyrano[2,3-d]pyrimidine derivatives." Collection of Czechoslovak Chemical Communications 54, no. 5 (1989): 1336–45. http://dx.doi.org/10.1135/cccc19891336.

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The starting 2-amino-5-ethoxycarbonyl-6-chloromethyl-4-(2-furyl)-3-cyano-4H-pyran (I) afforded on condensation with triethoxymethane 2-ethoxymethylenamino-4H-pyran II; treatment of the latter with ammonia yielded 2-formamidino-3-cyano-4H-pyran III, which, when heated in dilute ethanol, cyclized to 4-amino-6-ethoxycarbonyl-5-(2-furyl)-7-chloromethyl-4H-pyrano[2,3-d]pyrimidine (IV). Compound IV reacted with alkyl- or arylamines to give substituted 5H,6H,8H-pyrrolo[3',4':5,6]-4H-pyrano[2,3-d]pyrimidines VI, one of which (VIb, R = p-CH3C6H4) was alternatively obtained from 2-formamidino-4H-pyrano

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13

Mahmoud, M. R., A. A. Shalaby, T. A. Gad, and A. A. El-Khamry. "A facile synthesis and heteroannulation of pyrido[2,3-d]pyrimidine and related heterocyclic systems." Journal of Chemical Research 2009, no. 10 (2009): 612–15. http://dx.doi.org/10.3184/030823409x12523324765777.

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7-Amino-1,2,3,4-tetrahydro-4-oxo-2-thioxo-5-(3,4,5-trimethoxyphenyl)pyrido[2,3- d]pyrimidine (1) was prepared and reacted with methyl iodide and ethyl chloroacetate to give the S-alkylated products 2 and 3, respectively. The reaction of 1 or 3 with hydrazine hydrate yielded the same 2-hydrazino derivative 4. Treatment of 4 with 2,4-pentanedione, 2-acetylcyclohexanone and ethyl acetoacetate afforded the corresponding pyrazolylpyrido[2,3- d]pyrimidine derivatives (5–7), while phthalic anhydride gave the phthalazinyl compound 8. Ethoxymethylenemalononitrile with the hydrazine 4 formed the fused 1

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14

Kh. Ahmed, Essam, and Mohamed A. Ameen. "Synthesis of thiopyrano[4″,3″:4′,5′]pyrido[3′,2′:4,5]furo[3,2-d]pyrimidines." Chinese Chemical Letters 21, no. 6 (2010): 669–73. http://dx.doi.org/10.1016/j.cclet.2009.12.010.

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15

Quinn, RJ, PJ Scammells, CHL Kennard, and G. Smith. "Synthesis of 2-Substituted Pyrazolo[3,4-d]pyrimidines." Australian Journal of Chemistry 44, no. 12 (1991): 1795. http://dx.doi.org/10.1071/ch9911795.

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The reaction of 1-acetyl-2-phenylhydrazine with ethoxymethylenemalononitrile yielded [(4-cyano-1-phenylpyrazol-3-yl)aminomethylene]propanedinitrile. Hydrolysis followed by annulation with methyl isocyanate provided a synthetic route to 2-phenylpyrazolo[3,4-d]pyrimidines.

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16

Loidreau, Yvonnick, Pascal Marchand, Carole Dubouilh-Benard, Marie-Renée Nourrisson, Muriel Duflos, and Thierry Besson. "First synthesis of 4-aminopyrido[2′,3′:4,5]furo[3,2-d]pyrimidines." Tetrahedron Letters 53, no. 8 (2012): 944–47. http://dx.doi.org/10.1016/j.tetlet.2011.12.042.

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17

Nasr, Magda N., and Magdy M. Gineinah. "Pyrido [2, 3-d]pyrimidines and Pyrimido[5′, 4′:5, 6]pyrido[2, 3-d]pyrimidines as New Antiviral Agents: Synthesis and Biological Activity." Archiv der Pharmazie 335, no. 6 (2002): 289. http://dx.doi.org/10.1002/1521-4184(200208)335:6<289::aid-ardp289>3.0.co;2-z.

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18

Halim, Md E., K. Akhter, SM Ahmed, Md Al Amin Hossain, and UKR Romman. "One pot synthesis of Biginelli 3,4-dihydro-1H-pyrimidin-2-ones and 1,2,3,4-tetrahydro pyrimidines." Bangladesh Journal of Scientific and Industrial Research 55, no. 3 (2020): 173–80. http://dx.doi.org/10.3329/bjsir.v55i3.49390.

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A simple and practical route for the Biginelli cyclocondensation reaction using anhydrous ZnCl2 as a catalyst in n-heptane-toluene medium by reaction of substituted benzaldehydes,1a-d (1a=2-ClC6H4-, 1b=2-BrC6H4- and 1c=4-ClC6H4-,1d=2-H3CC6H4-) with 1, 3-dicarbonyl compounds, 2a-b (2a= ethyl acetoacetate and 2b= acetylacetone) and urea or thiourea, 3a-b to give the corresponding Biginelli 3,4-dihydro- 1H-pyrimidin-2-ones and 1,2,3,4-tetrahydro pyrimidines, 4a-d. The structures of the compounds 4a-d were confirmed by their ultraviolet, infrared, 1H NMR, 13C NMR spectra and elemental analyses.&#x

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19

Ahmed, Essam Kh, and Mohamed A. Ameen. "ChemInform Abstract: Synthesis of Thiopyrano[4′′,3′′:4′,5′]pyrido[3′,2′:4,5]furo[3,2-d]pyrimidines." ChemInform 41, no. 43 (2010): no. http://dx.doi.org/10.1002/chin.201043163.

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20

Garaeva, Lydmila D., Irina V. Yartseva, and Stalina Ya Melnik. "Studies on Glycosides of 3, 4, 6-Trisubstituted Pyrazolo-[3, 4-D]Pyrimidines. Synthesis of 2′-Deoxyribonucleosides." Nucleosides and Nucleotides 10, no. 6 (1991): 1295–303. http://dx.doi.org/10.1080/07328319108047063.

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21

Nagashree, A. S., K. Kusuma, M. S. Latha, A. S. Sowmyashree, and V. P. Vaidya. "Synthesis and Pharmacological activities of 2-Substituted-3-Hydro/Aryl-3, 4-Dihydro-4-Oxo-Naphtho[2,1-B] Furo [3,2-D] Pyrimidines. (Research Article)." International Journal of Pharmacy and Biological Sciences 11, no. 1 (2021): 48–55. http://dx.doi.org/10.21276/ijpbs.2021.11.1.6.

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22

DAVE, C. G., P. R. SHAH, P. S. PANDYA, and G. K. SHAH. "ChemInform Abstract: Pyridopyrimidines. Part 6. Synthesis and Reactions of 4-Iminopyrido-(2, 3-d)pyrimidines and 3H-2-Thioxopyrido(2,3-d)pyrimidin-4-ones." ChemInform 22, no. 31 (2010): no. http://dx.doi.org/10.1002/chin.199131209.

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23

Abdelhamid, Abdou O., and Sobhi M. Gomha. "Synthesis of New Pyrazolo[1,5-a]pyrimidine, Triazolo[4,3-a]pyrimidine Derivatives, and Thieno[2,3-b]pyridine Derivatives from Sodium 3-(5-Methyl-1-phenyl-1H-pyrazol-4-yl)-3-oxoprop-1-en-1-olate." Journal of Chemistry 2013 (2013): 1–7. http://dx.doi.org/10.1155/2013/327095.

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Condensation of sodium 3-oxo-3-(1-phenyl-1H-pyrazol-4-yl)prop-1-en-1-olate (2) with several heterocyclic amines, cyanoacetamide, cyanothioacetamide, and 2-cyanoacetohydrazide gives pyrazolo[1,5-a]pyrimidines (5a–d), pyrido[2′,3′:3,4]pyrazolo[1,5-a]pyrimidine (9), benzo[4,5]imidazo[1,2-a]pyrimidine (10), [1,2,4]triazolo[1,5-a]pyrimidine (11), and pyridine derivatives (12–14). Also, thieno[2,3-b]pyridines (15–18) were synthesized via pyridinethione (13) withα-halo ketones andα-halo ester. Structures of the newly synthesized compounds were elucidated by elemental analysis, spectral data, alternat

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24

Loidreau, Yvonnick, Pascal Marchand, Carole Dubouilh-Benard, Marie-Renee Nourrisson, Muriel Duflos, and Thierry Besson. "ChemInform Abstract: First Synthesis of 4-Aminopyrido[2′,3′:4,5]furo[3,2-d]pyrimidines." ChemInform 43, no. 24 (2012): no. http://dx.doi.org/10.1002/chin.201224171.

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TAHA, M. L., H. B. LAZREK, J. L. BARASCUT, and J. L. IMBACH. "ChemInform Abstract: Synthesis of Some 4-Substituted 1-((2-Hydroxyethoxy)methyl)pyrazolo(3, 4-d)pyrimidines." ChemInform 27, no. 34 (2010): no. http://dx.doi.org/10.1002/chin.199634250.

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26

Kidwai, Mazaahir, and Alkal Mishra. "An expeditious synthesis of 3, 4-dihydro-benzo[2,3-d]pyrimidines using inorganic solid supports." Journal of the Serbian Chemical Society 69, no. 4 (2004): 247–54. http://dx.doi.org/10.2298/jsc0404247k.

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Aseries of novel 5-substituted-8-cyano-4,6,7-triphenyl-3,4-dihydrobenzo [2,3-d]pyrimidines were synthesized by the condensation of 6-substituted-2-amino 1-benzoyl-3-cyano-5-hydroxy-4,5-diphenyl-1,3-cyclohexadiene and formamide using inorganic solid supports under microwaves. Some of the compounds were found to be effective against some fungal and bacterial strains.

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27

Bodige, Srinu, Parameshwar Ravula, Kali Charan Gulipalli, et al. "Design, Synthesis and Biological Evaluation of Novel Urea and Thiourea Bearing thieno[3,2-d]-pyrimidines as PI3 Kinase Inhibitors." Anti-Cancer Agents in Medicinal Chemistry 18, no. 6 (2018): 891–902. http://dx.doi.org/10.2174/1871520618666180209151018.

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Background: Phosphatidylinositol-3-kinase α (PI3Kα) is a ubiquitous intracellular enzyme, mainly involved in intracellular signaling pathways, promotes cellular growth, proliferation, and differentiation. Therefore, inhibition of PI3K can be a hotspot in molecular targeted therapy for the treatment of cancer. Methods: The present research work involves molecular docking studies performed to screen derivatives of urea and thiourea bearing thieno [3,2-d]-pyrimidines against the active site of PI3K enzyme using MOE.2008.10. The designed structures (6a-f) and (7a-j) were synthesized by the facile

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28

Dabaeva, V. V., A. S. Noravyan, and B. D. Enokyan. "Synthesis of dihydro-10H-pyrano[3?,4?: 5,6]pyrido[3,2:4?,5?]-thieno[3?,2?-d][3,1]oxazines and pyrimidines." Chemistry of Heterocyclic Compounds 31, no. 2 (1995): 219–22. http://dx.doi.org/10.1007/bf01169683.

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29

Mkrtchyan, A. P., A. Sh Oganisyan, Art Sh Oganisyan, and A. S. Noravyan. "Derivatives of Condensed Thienopyrimidines. 22. Synthesis of 2-Substituted 4-Thioxopyrano[4′,3′:4,5]thieno[2,3-d]pyrimidines." Chemistry of Heterocyclic Compounds 41, no. 2 (2005): 235–37. http://dx.doi.org/10.1007/s10593-005-0133-4.

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30

Suresh, Lingala, Y. Poornachandra, S. Kanakaraju, C. Ganesh Kumar, and G. V. P. Chandramouli. "One-pot three-component domino protocol for the synthesis of novel pyrano[2,3-d]pyrimidines as antimicrobial and anti-biofilm agents." Organic & Biomolecular Chemistry 13, no. 26 (2015): 7294–306. http://dx.doi.org/10.1039/c5ob00693g.

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A simple and facile synthesis of a series of novel pyrano[2,3-d]pyrimidines have been achieved successfullyviaone-pot three-component reaction of 2-amino-7-methyl-5-oxo-4-phenyl-4,5-dihydropyrano[4,3-b]pyran-3-carbonitriles, DMF-DMA and arylamines.

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31

Kurasawa, Yoshihisa, Yumiko Kamigaki, Ho Sik Kim, et al. "Synthesis and13C-NMR study of novel pyrazolo[5′,1′:3, 4][1, 2, 4]triazino[5, 6-d]pyrimidines." Journal of Heterocyclic Chemistry 26, no. 3 (1989): 853–56. http://dx.doi.org/10.1002/jhet.5570260363.

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DABAEVA, V. V., A. S. NORAVYAN, and B. D. ENOKYAN. "ChemInform Abstract: Synthesis of Dihydro-10H-pyrano(3′,4′:5,6)pyrido(3,2:4′′,5′′)thieno(3′′ ,2′′-d) oxazines(3,1) and -pyrimidines." ChemInform 26, no. 38 (2010): no. http://dx.doi.org/10.1002/chin.199538183.

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33

Ameen, Mohamed A. "Novel Selective 5-HT3 Receptor Ligands: Facile Generation Methods for 2-Amino- and 4-Aminopyrido[4’,3’:4,5]thieno[2,3-d]pyrimidines." Zeitschrift für Naturforschung B 61, no. 10 (2006): 1234–38. http://dx.doi.org/10.1515/znb-2006-1008.

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This work reports on the synthesis of new 2-amino- and 4-aminopyridothienopyrimidines, with a view to identify potent and selective ligands for the 5-HT3 receptor, starting from derivatives of 2-aminothiophene-3-carboxylic ester, -3-carboxamide, or 2-amino-3-cyanothiophene.

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34

Ahluwalia, V. K., Rakesh Kumar, Anju Khurana, and Rita Bhatla. "A convenient synthesis of 1,3-diaryl-1,2,3,4,-tetrahydro-5,7,7-trimethyl-4-oxo-2-thioxo-7H-pyrano[ 2 ,3-d ]pyrimidines." Tetrahedron 46, no. 11 (1990): 3953–62. http://dx.doi.org/10.1016/s0040-4020(01)90530-7.

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35

Taltavull, Joan, Jordi Serrat, Jordi Gràcia, et al. "Synthesis and Biological Activity of Pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidines as Phosphodiesterase Type 4 Inhibitors." Journal of Medicinal Chemistry 53, no. 19 (2010): 6912–22. http://dx.doi.org/10.1021/jm100524j.

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Abed, Nosrat Mustafa, Nadia Sobhy Ibrahim, and Mohamed Helmy Elnagdi. "Studies on Heterocyclic Enamines: New Synthesis of Pyrano[2,3-b]pyndine, Pyrano[2,3-d]pyrimidine and Pyrano[2,3-c]pyrazole Derivatives." Zeitschrift für Naturforschung B 41, no. 7 (1986): 925–28. http://dx.doi.org/10.1515/znb-1986-0721.

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AbstractA variety of novel pyrano[2,3-d]pyrimidines could be obtained via reaction of ethyl 2-amino- 3-cyano-6-methylpyran-4-carboxylate with a variety of reagents. Evidence for the existance of this pyran derivative as a ring chain tautom er is presented.

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37

Narsaiah, B., A. Sivaprasad, and R. V. Venkataratnam. "Synthesis of novel 2,7-disubstituted-3-amino-9-trifluoromethyl-4-oxo-4H-pyrido-[3',2':4,5]-furo-[3,2-d]-(1,3)-pyrimidines." Journal of Fluorine Chemistry 69, no. 2 (1994): 139–43. http://dx.doi.org/10.1016/0022-1139(94)03079-0.

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38

Ahmed, E. Kh, A. M. N. Gohar, and M. A. Ameen. "ChemInform Abstract: Synthesis of New Pyrido[4′,3′:4,5]thieno[2,3-d]-1,2,4-triazolo[3,4-c]pyrimidines and a 5,6-Dihydro-1,2,4-triazolo[4′′,3′′:1′,2′]pyrido[4′,3′:4,5]thieno [2,3-d]pyrimidine Ring System." ChemInform 31, no. 20 (2010): no. http://dx.doi.org/10.1002/chin.200020129.

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39

Mkrtchyan, A. P., and A. S. Noravyan. "Derivatives of condensed thieno[2,3-d]-pyrimidines. 20. Synthesis of 2-substituted 5,6-dihydro-8H-pyrano[4′,3′:4,5]thieno[2,3-d]pyrimidin-4(3H)-ones and 5,6,7,8-tetrahydrobenzo-[b]thieno[2,3-d]pyrimidin-4-ones." Chemistry of Heterocyclic Compounds 42, no. 3 (2006): 392–95. http://dx.doi.org/10.1007/s10593-006-0098-y.

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40

Veselovská, Lucia, Radek Pohl, Eva Tloušt′ová, et al. "Pyrido-Fused Deazapurine Bases: Synthesis and Glycosylation of 4-Substituted 9H-Pyrido[2′,3′:4,5]- and Pyrido[4′,3′:4,5]pyrrolo[2,3-d]pyrimidines." ACS Omega 5, no. 40 (2020): 26278–86. http://dx.doi.org/10.1021/acsomega.0c04302.

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41

Mkrtchyan, A. P., A. S. Noravyan, and V. M. Petrosyan. "ChemInform Abstract: Derivatives of Condensed Thieno[2,3-d]pyrimidines. Part 15. Synthesis of 2-Substituted 3-Amino-6,6-dimethyl-5,6-dihydro-8H-pyrano[4′,3′:4,5]thieno [2,3-d]pyrimidin-4-ones." ChemInform 33, no. 43 (2010): no. http://dx.doi.org/10.1002/chin.200243187.

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42

Blanco, Gerardo, José M. Quintela, and Carlos Peinador. "Synthesis of new heteroaromatic nitrogen ligands: Pyrimido-[4″,5″:4′,5′]-thieno[3′,2′:4,5]thieno[3,2-d]pyrimidines and 1,2,3-triazine[4″,5″:4′,5′]thieno[3′,2′:4,5]thieno[3,2-d]-1,2,3-triazines." Journal of Heterocyclic Chemistry 43, no. 4 (2006): 1051–56. http://dx.doi.org/10.1002/jhet.5570430435.

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43

Sirakanyan, S. N., A. A. Ovakimyan, A. S. Noravyan, et al. "Synthesis and Anticonvulsive Activity of 7-Amino-Substituted Cyclopenta[4′,5′]-pyrido[3′,2′:4,5]furo[3,2-d]pyrimidines." Pharmaceutical Chemistry Journal 47, no. 3 (2013): 130–34. http://dx.doi.org/10.1007/s11094-013-0910-9.

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44

Fattahi, Mehri, Abolghasem Davoodnia, Mehdi Pordel, S. Ali Beyramabadi, and Niloofar Tavakoli-Hoseini. "Isolation of intermediates in the synthesis of new 3,4-dihydro-2H-chromeno[2,3-d]pyrimidines." Zeitschrift für Naturforschung B 73, no. 8 (2018): 557–63. http://dx.doi.org/10.1515/znb-2018-0042.

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AbstractReaction of N-alkyl-2-imino-2H-chromene-3-carboxamides with dimethyl acetylenedicarboxylate (DMAD) in the presence of sodium carbonate as catalyst in refluxing ethanol gave new tricyclic products identified as methyl 3-alkyl-2-(2-methoxy-2-oxoethyl)-4-oxo-3,4-dihydro-2H-chromeno[2,3-d]pyrimidine-2-carboxylates. In the absence of sodium carbonate, dimethyl 2-((E)-3-(alkylcarbamoyl)-2H-chromen-2-ylideneamino)fumarates were isolated as intermediates. These intermediates could be successfully converted to the same new tricyclic products by heating in ethanol containing sodium carbonate. Al

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45

Zaki, Remon M., Adel M. Kamal El-Dean, Shaban M. Radwan, and Ahmed F. Saber. "Efficient synthesis, reactions and spectral characterization of pyrazolo[4’,3’:4,5]thieno[3,2-d] pyrimidines and related heterocycles." Heterocyclic Communications 25, no. 1 (2019): 39–46. http://dx.doi.org/10.1515/hc-2019-0004.

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AbstractNew pyrazolothienopyrimidines were synthesized. The key intermediate 4-aminothieno[2,3-c]pyrazole-5-carbonitrile 1 was converted to the chloroacetyl amino derivative 2 followed by nucleophilic substitution and Dimorth rearrangement upon treatment with nitrogen nucleophiles to give the pyrimidinones 3a-c. Treatment of 3a with formaldehyde and with triethyl orthoformate afforded the respective tetracyclic derivatives 4 and 5. Condensation of the amino group in the o-aminocarbonitrile 1 with triethyl orthoformate followed by cycloaddition reaction with hydrazine led to the formation of py

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46

Paronikyan, E. G., Sh Sh Dashyan, N. S. Minasyan, and G. M. Stepanyan. "Synthesis of 5,8-Diamino-Substituted Pyrano[4″,3″:4′,5′]pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidines and Pyrimido[4′,5′:4,5]thieno[2,3-c]isoquinolines." Russian Journal of Organic Chemistry 52, no. 4 (2016): 576–81. http://dx.doi.org/10.1134/s1070428016040187.

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47

Solomyannyi, R. N., S. R. Slivchuk, A. N. Vasilenko, E. B. Rusanov, and V. S. Brovarets. "Synthesis of 3-amino-1-benzyl-4-benzenesulfonyl-2-carbonitrilo-1H-pyrrole and preparation of related pyrrolo[3,2-d]pyrimidines." Russian Journal of General Chemistry 82, no. 2 (2012): 317–22. http://dx.doi.org/10.1134/s1070363212020235.

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48

Bakhite, E. A., A. G. Al-Sehemi, and Y. Yamada. "Synthesis of novel pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidines, pyrido[3″,2″:4′,5′]thieno[3′,2′:4,5]pyrimido[l,6-a]benzimidazoles and related fused systems." Journal of Heterocyclic Chemistry 42, no. 6 (2005): 1069–77. http://dx.doi.org/10.1002/jhet.5570420606.

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49

NARSAIAH, B., A. SIVAPRASAD, and R. V. VENKATARATNAM. "ChemInform Abstract: Synthesis of Novel 2,7-Disubstituted-3-amino-9-trifluoromethyl-4-oxo- 4H-pyrido-(3′,2′:4,5)-furo-(3,2-d)-(1,3)-pyrimidines." ChemInform 26, no. 17 (2010): no. http://dx.doi.org/10.1002/chin.199517159.

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50

Bakhite, Etify A., Abdu E. Abdel-Rahman, and Elham A. Al-Taifi. "Fluorine-Containing Heterocycles: Part I. Synthesis of New 7-(2-thienyl)-9-Trifluoromethylpyrido[3′,2′:4,5]Thieno[3,2-d]Pyrimidines and Related Fused Tetracyclic Systems." Journal of Chemical Research 2005, no. 3 (2005): 147–54. http://dx.doi.org/10.3184/0308234054213726.

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3-amino-6-(2-thienyl)-4-trifluoromethylthieno[2,3-b]pyridine-2-carboxamide (3) and 2-carbonitrile analogue 5 were prepared by reaction of 3-cyano-6-(2-thienyl)-4-trifluoromethylpyridine-2(1H)-thione (1) with chloroacetamide or chloroacetonitrile respectively. Heating compound 3 with triethyl orthoformate led to the formation of pyridothienopyrimidinone derivative 6. Reaction of 6 with phosphorus oxychloride produced 4-chloropyrimidine derivative 7 which underwent some nucleophilic displacements upon treatment with thiourea, piperidine, morpholine or hydrazine hydrate to give the target 4-subst

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