메뉴 건너뛰기




Volumn 15, Issue 3, 2011, Pages 697-705

Unexpected deviation from diene behaviour of uracil amidine: Towards synthesis of some pyrido[2,3-d]pyrimidine derivatives

Author keywords

Cycloaddition reaction; Heterocycles; Pyridopyrimidines; Silica gel

Indexed keywords

5,8 DIHYDROPYRIDO[2,3 D]PYRIMIDINE; ALKENE DERIVATIVE; AMIDINE; PYRIDO[2,3 D]PYRIMIDINE DERIVATIVE; PYRIMIDINE; UNCLASSIFIED DRUG; URACIL AMIDINE;

EID: 80051594895     PISSN: 13811991     EISSN: 1573501X     Source Type: Journal    
DOI: 10.1007/s11030-010-9293-y     Document Type: Article
Times cited : (21)

References (30)
  • 1
    • 0026525079 scopus 로고
    • Reactivity of nitrile oxides toward the 5,6-double bond of uracil derivatives: Synthesis of some 5-aroylpyrimidine nucleoside oximes
    • 10.1021/jo00030a011 10.1021/jo00030a011 1:CAS:528:DyaK38XhtVKltbo%3D
    • JN Kim EK Ryu 1992 Reactivity of nitrile oxides toward the 5,6-double bond of uracil derivatives: synthesis of some 5-aroylpyrimidine nucleoside oximes J Org Chem 57 1088 1092 10.1021/jo00030a011 10.1021/jo00030a011 1:CAS:528:DyaK38XhtVKltbo%3D
    • (1992) J Org Chem , vol.57 , pp. 1088-1092
    • Kim, J.N.1    Ryu, E.K.2
  • 2
    • 0030952516 scopus 로고    scopus 로고
    • Reactivity of lithium trimethylsilyldiazomethane and diazomethane toward the 5,6-double bond of uracil and uridine derivatives
    • DOI 10.1016/S0040-4020(97)00402-X, PII S004040209700402X
    • R Saladino L Stasi C Crestini R Nicoletti M Botta 1997 Reactivity of lithium trimethylsilyldiazomethane and diazomethane toward the 5,6-double bond of uracil and uridine derivatives Tetrahedron 53 7045 7056 10.1016/S0040- 4020(97)00402-x 10.1016/S0040-4020(97)00402-X 1:CAS:528:DyaK2sXjsV2gurc%3D (Pubitemid 27208421)
    • (1997) Tetrahedron , vol.53 , Issue.20 , pp. 7045-7056
    • Saladino, R.1    Stasi, L.2    Crestini, C.3    Nicoletti, R.4    Botta, M.5
  • 3
    • 33744466538 scopus 로고    scopus 로고
    • One-pot synthesis of novel 1H-pyrimido[4,5-c][1,2]diazepines and pyrazolo[3,4-d]pyrimidines
    • DOI 10.1186/1860-5397-2-5
    • D Prajapati PP Baruah BJ Gogoi JS Sandhu 2006 One-pot synthesis of novel 1H-pyrimido[4,5-c][1,2] diazepines and pyrazolo[3,4-d]pyrimidines Beilstein J Org Chem 2 5 10.1186/1860-5397-2-5 16556308 10.1186/1860-5397-2-5 (Pubitemid 43807005)
    • (2006) Beilstein Journal of Organic Chemistry , vol.2 , pp. 5
    • Prajapati, D.1    Baruah, P.P.2    Gogoi, B.J.3    Sandhu, J.S.4
  • 4
    • 0000137644 scopus 로고
    • Pyrimido[4,5-d]pyrimidines, pyrimido[4',5':4,5]pyrimido[6,1-a]azepines, and an imidazo [5,1-f][1,2,4]triazine by three-component reactions
    • 10.3987/COM-92-S(T)102 10.3987/COM-92-S(T)102 1:CAS:528: DyaK2cXhtlCgsLw%3D
    • H Wamhoff A Schmidt 1993 Pyrimido[4,5-d]pyrimidines, pyrimido[4',5':4,5] pyrimido[6,1-a]azepines, and an imidazo [5,1-f][1,2,4]triazine by three-component reactions Heterocycles 35 1055 1066 10.3987/COM-92-S(T)102 10.3987/COM-92-S(T)102 1:CAS:528:DyaK2cXhtlCgsLw%3D
    • (1993) Heterocycles , vol.35 , pp. 1055-1066
    • Wamhoff, H.1    Schmidt, A.2
  • 5
    • 0001341315 scopus 로고
    • N-bromosuccinimide in heterocyclic synthesis. synthesis of pyrazolo[3,4-d]pyrimidines, pyrimido[5,4-e]triazines, and pyrimido[4,5-c] pyridazines from 6-arylidenehydrazino-1,3-dimethyluracil derivatives
    • 10.1002/jhet.5570210408 10.1002/jhet.5570210408 1:CAS:528:DyaL2MXmtl2i
    • H Kanazawa S Nishigaki K Senga 1984 N-bromosuccinimide in heterocyclic synthesis. synthesis of pyrazolo[3,4-d]pyrimidines, pyrimido[5,4-e]triazines, and pyrimido[4,5-c]pyridazines from 6-arylidenehydrazino-1,3-dimethyluracil derivatives J Heterocycl Chem 21 969 974 10.1002/jhet.5570210408 10.1002/jhet.5570210408 1:CAS:528:DyaL2MXmtl2i
    • (1984) J Heterocycl Chem , vol.21 , pp. 969-974
    • Kanazawa, H.1    Nishigaki, S.2    Senga, K.3
  • 6
    • 0000295753 scopus 로고    scopus 로고
    • Synthesis of pyrido[2,3-d]pyrimidines via palladium-catalyzed coupling reaction followed by electrocyclic reaction
    • KY Rho JH Kim SH Kim CM Yoon 1998 Synthesis of pyrido[2,3-d]pyrimidines via a palladium-catalyzed coupling reaction followed by an electrocyclic reaction Heterocycles 48 2521 2528 10.3987/COM-98-8295 10.3987/COM-98-8295 1:CAS:528:DyaK1MXltVWisw%3D%3D (Pubitemid 128659099)
    • (1998) Heterocycles , vol.48 , Issue.12 , pp. 2521-2528
    • Rho, K.Y.1    Kim, J.H.2    Kim, S.H.3    Yoon, C.M.4
  • 8
    • 0029042466 scopus 로고
    • 6-Substituted-2,4-diamino-5-methylpyrido[2,3-d]pyrimidines as inhibitors of dihydrofolate reductases from pneumocystis carinii and toxoplasma gondii and as antitumor agents
    • 10.1021/jm00010a022 7752201 10.1021/jm00010a022 1:CAS:528: DyaK2MXltlyru7k%3D
    • A Gangjee A Vasudevan SF Queener RL Kisliuk 1995 6-Substituted-2,4- diamino-5-methylpyrido[2,3-d]pyrimidines as inhibitors of dihydrofolate reductases from pneumocystis carinii and toxoplasma gondii and as antitumor agents J Med Chem 38 1778 1785 10.1021/jm00010a022 7752201 10.1021/jm00010a022 1:CAS:528:DyaK2MXltlyru7k%3D
    • (1995) J Med Chem , vol.38 , pp. 1778-1785
    • Gangjee, A.1    Vasudevan, A.2    Queener, S.F.3    Kisliuk, R.L.4
  • 9
    • 0029990447 scopus 로고    scopus 로고
    • 2,4-Diamino-5-deaza-6-substituted pyrido[2,3-d]pyrimidine antifolates as potent and selective nonclassical inhibitors of dihydrofolate reductases
    • DOI 10.1021/jm950786p
    • A Gangjee A Vasudevan SF Queener RL Kisliuk 1996 2,4-Diamino-5-deaza-6- substituted pyrido[2,3-d]pyrimidine antifolates as potent and selective nonclassical inhibitors of dihydrofolate reductases J Med Chem 39 1438 1446 10.1021/jm950786p 8691474 10.1021/jm950786p 1:CAS:528:DyaK28XhsVyhu78%3D (Pubitemid 26112709)
    • (1996) Journal of Medicinal Chemistry , vol.39 , Issue.7 , pp. 1438-1446
    • Gangjee, A.1    Vasudevan, A.2    Queener, S.F.3    Kisliuk, R.L.4
  • 10
    • 1242333920 scopus 로고
    • Eur Patent 351058
    • Coates WJ (1990) Eur Patent 351058; Chem Abstr 1990, 113, 40711
    • (1990) Chem Abstr , vol.113 , pp. 40711
    • Coates, W.J.1
  • 11
    • 80051588717 scopus 로고
    • US Patent 3830812; FMC Corp. Chem Abstr 1974, 81, 136174
    • Ramsey AA (1974) US Patent 3830812; FMC Corp. Chem Abstr 1974, 81, 136174
    • (1974)
    • Ramsey, A.A.1
  • 12
    • 33947473659 scopus 로고
    • Pyrimido[4,5-d]pyrimidines. Part i
    • 10.1021/ja01506a038 10.1021/ja01506a038 1:CAS:528:DyaF3MXjtlWjtQ%3D%3D
    • EC Taylor RJ Knopf RF Meyer A Holmes ML Hoefle 1960 Pyrimido[4,5-d] pyrimidines. Part I J Am Chem Soc 82 5711 5718 10.1021/ja01506a038 10.1021/ja01506a038 1:CAS:528:DyaF3MXjtlWjtQ%3D%3D
    • (1960) J Am Chem Soc , vol.82 , pp. 5711-5718
    • Taylor, E.C.1    Knopf, R.J.2    Meyer, R.F.3    Holmes, A.4    Hoefle, M.L.5
  • 13
    • 0000856886 scopus 로고
    • Synthesis of 6-phenylaminofuro[2,3-d]pyrimidine-2,4(1H, 3H)-diones from barbiturylbenzylidenes and isonitriles
    • 10.3987/COM-92-5989 10.3987/COM-92-5989 1:CAS:528:DyaK38XltlWitrk%3D
    • JD Figueroa-Villar CL Carneiro ER Cruz 1992 Synthesis of 6-phenylaminofuro[2,3-d]pyrimidine-2,4(1H, 3H)-diones from barbiturylbenzylidenes and isonitriles Heterocycles 34 891 894 10.3987/COM-92-5989 10.3987/COM-92-5989 1:CAS:528:DyaK38XltlWitrk%3D
    • (1992) Heterocycles , vol.34 , pp. 891-894
    • Figueroa-Villar, J.D.1    Carneiro, C.L.2    Cruz, E.R.3
  • 14
    • 1242289062 scopus 로고
    • Eur Patent 163599
    • Kitamura N, Onishi A (1984) Eur Patent 163599; Chem Abstr 1984, 104, 186439
    • (1984) Chem Abstr , vol.104 , pp. 186439
    • Kitamura, N.1    Onishi, A.2
  • 15
  • 16
    • 0023803012 scopus 로고
    • 6-[(dimethylamino)methylene]amino-1,3-dimethyluracil: A versatile aza-diene substrate for cycloaddition and Michael-type reactions
    • 10.1016/S0040-4039(00)80505-5 10.1016/S0040-4039(00)80505-5 1:CAS:528:DyaL1MXktl2jtb0%3D
    • EB Walsh ZN Jue G Fang H Wamhoff 1988 6-[(dimethylamino)methylene]amino- 1,3-dimethyluracil: A versatile aza-diene substrate for cycloaddition and Michael-type reactions Tetrahedron Lett 29 4401 4404 10.1016/S0040-4039(00) 80505-5 10.1016/S0040-4039(00)80505-5 1:CAS:528:DyaL1MXktl2jtb0%3D
    • (1988) Tetrahedron Lett , vol.29 , pp. 4401-4404
    • Walsh, E.B.1    Jue, Z.N.2    Fang, G.3    Wamhoff, H.4
  • 17
    • 33646834745 scopus 로고    scopus 로고
    • Regiospecific one-pot synthesis of pyrimido[4,5-d]pyrimidine derivatives in the solid state under microwave irradiations
    • DOI 10.1016/j.bmcl.2006.03.088, PII S0960894X06003945
    • D Prajapati M Gohain AJ Thakur 2006 Regiospecific one-pot synthesis of pyrimido[4,5-d]pyrimidine derivatives in the solid state under microwave irradiations Bioorg Med Chem Lett 16 3537 3540 10.1016/j.bmcl.2006.03.088 16650990 10.1016/j.bmcl.2006.03.088 1:CAS:528:DC%2BD28XkvF2isbk%3D (Pubitemid 43777093)
    • (2006) Bioorganic and Medicinal Chemistry Letters , vol.16 , Issue.13 , pp. 3537-3540
    • Prajapati, D.1    Gohain, M.2    Thakur, A.J.3
  • 18
    • 13544272928 scopus 로고    scopus 로고
    • Studies on 6-[(dimethylamino)methylene]aminouracil: A facile one-pot synthesis of novel pyrimido[4,5-d]pyrimidine derivatives
    • DOI 10.1016/j.tetlet.2005.01.047
    • D Prajapati AJ Thakur 2005 Studies on 6-[(dimethylamino)methylene] aminouracil: a facile one-pot synthesis of novel pyrimido[4,5-d]pyrimidine derivatives Tetrahedron Lett 46 1433 1436 10.1016/j.tetlet.2005.01.047 10.1016/j.tetlet.2005.01.047 1:CAS:528:DC%2BD2MXht1CltrY%3D (Pubitemid 40220292)
    • (2005) Tetrahedron Letters , vol.46 , Issue.9 , pp. 1433-1436
    • Prajapati, D.1    Thakur, A.J.2
  • 19
    • 2942750464 scopus 로고    scopus 로고
    • A facile microwave induced one-pot synthesis of novel pyrimido[4,5-d] pyrimidines and pyrido[2,3-d]pyrimidines under solvent-free conditions
    • Gohain M, Prajapati D, Gogoi BJ, Sandhu JS (2004) A facile microwave induced one-pot synthesis of novel pyrimido[4,5-d]pyrimidines and pyrido[2,3-d]pyrimidines under solvent-free conditions. Synlett 1179-1182. doi: 10.1055/s-2004-825601 (Pubitemid 38797655)
    • (2004) Synlett , Issue.7 , pp. 1179-1182
    • Gohain, M.1    Prajapati, D.2    Gogoi, B.J.3    Sandhu, J.S.4
  • 20
    • 0036104080 scopus 로고    scopus 로고
    • Studies on 6-[(dimethylamino)methylene]aminouracil: A facile one-pot synthesis of novel pyrido[2,3-d]pyrimidines
    • P Saikia AJ Thakur D Prajapati JS Sandhu 2002 Studies on 6-[(dimethylamino)methylene]aminouracil: a facile one-pot synthesis of novel pyrido[2,3-d]pyrimidines Indian J Chem Sect B 41 804 807
    • (2002) Indian J Chem Sect B , vol.41 , pp. 804-807
    • Saikia, P.1    Thakur, A.J.2    Prajapati, D.3    Sandhu, J.S.4
  • 21
    • 0141957353 scopus 로고    scopus 로고
    • A novel three-component one-pot synthesis of pyrano[2,3-d]pyrimidines and pyrido[2,3-d]pyrimidines using microwave heating in the solid state
    • DOI 10.1016/j.tetlet.2003.09.063
    • I Devi BSD Kumar PJ Bhuyan 2003 A novel three-component one-pot synthesis of pyrano[2,3-d]pyrimidines and pyrido[2,3-d]pyrimidines using microwave heating in the solid state Tetrahedron Lett 44 8307 8310 10.1016/j.tetlet.2003. 09.063 10.1016/j.tetlet.2003.09.063 1:CAS:528:DC%2BD3sXotVOrtbw%3D (Pubitemid 37238975)
    • (2003) Tetrahedron Letters , vol.44 , Issue.45 , pp. 8307-8310
    • Devi, I.1    Kumar, B.S.D.2    Bhuyan, P.J.3
  • 22
    • 34547163794 scopus 로고    scopus 로고
    • New strategy for the oxidation of Hantzsch 1,4-dihydropyridines and dihydropyrido[2,3-d]pyrimidines catalyzed by DMSO under aerobic conditions
    • DOI 10.1080/00397910701410442, PII 780557123
    • A Saini S Kumar JS Sandhu 2007 New strategy for the oxidation of hantzsch 1,4-dihydropyridines and dihydropyrido[2,3-d]pyrimidines catalyzed by DMSO under aerobic conditions Synth Commun 37 2317 2324 10.1080/00397910701410442 10.1080/00397910701410442 1:CAS:528:DC%2BD2sXotVOntbY%3D (Pubitemid 47123663)
    • (2007) Synthetic Communications , vol.37 , Issue.14 , pp. 2317-2324
    • Saini, A.1    Kumar, S.2    Sandhu, J.S.3
  • 23
    • 13244272071 scopus 로고    scopus 로고
    • Solid supported synthesis of structurally diverse dihydropyrido[2,3-d] pyrimidines using microwave irradiation
    • DOI 10.1016/j.tetlet.2004.12.109, PII S0040403904028321
    • A Agarwal PMS Chauhan 2005 Solid supported synthesis of structurally diverse dihydropyrido[2,3-d]pyrimidines using microwave irradiation Tetrahedron Lett 46 1345 1348 10.1016/j.tetlet.2004.12.109 10.1016/j.tetlet.2004.12.109 1:CAS:528:DC%2BD2MXosF2rtw%3D%3D (Pubitemid 40186755)
    • (2005) Tetrahedron Letters , vol.46 , Issue.8 , pp. 1345-1348
    • Agarwal, A.1    Chauhan, P.M.S.2
  • 24
    • 0000801859 scopus 로고
    • Metal-ion complexation of noncyclic poly(oxyethylene) derivatives. II. PMR studies of the complexation with alkali and alkaline-earth metal cations
    • 10.1246/bcsj.51.1294 10.1246/bcsj.51.1294 1:CAS:528:DyaE1cXksFalsL8%3D
    • S Yanagida K Takahashi M Okahara 1978 Metal-ion complexation of noncyclic poly(oxyethylene) derivatives. II. PMR studies of the complexation with alkali and alkaline-earth metal cations Bull Chem Soc Jpn 51 1294 1299 10.1246/bcsj.51.1294 10.1246/bcsj.51.1294 1:CAS:528:DyaE1cXksFalsL8%3D
    • (1978) Bull Chem Soc Jpn , vol.51 , pp. 1294-1299
    • Yanagida, S.1    Takahashi, K.2    Okahara, M.3
  • 25
    • 0000801858 scopus 로고
    • Metal-ion complexation of noncyclic poly(oxyethylene) derivatives. complexation in aprotic solvent and isolation of their solid complexes
    • 10.1246/bcsj.51.3111 10.1246/bcsj.51.3111 1:CAS:528:DyaE1MXps1OntA%3D%3D
    • S Yanagida K Takahashi M Okahara 1978 Metal-ion complexation of noncyclic poly(oxyethylene) derivatives. complexation in aprotic solvent and isolation of their solid complexes Bull Chem Soc Jpn 51 3111 3120 10.1246/bcsj.51.3111 10.1246/bcsj.51.3111 1:CAS:528:DyaE1MXps1OntA%3D%3D
    • (1978) Bull Chem Soc Jpn , vol.51 , pp. 3111-3120
    • Yanagida, S.1    Takahashi, K.2    Okahara, M.3
  • 26
    • 77950241808 scopus 로고    scopus 로고
    • Synthesis of N-bz-protected D-daunosamine and D-ristosamine by silica gel promoted intramolecular conjugate addition of trichloroacetimidates obtained from osmundalactone and its epimer
    • doi: 10.1002/ejoc.200901402
    • Matsushima Y, Kino J (2010) Synthesis of N-bz-protected D-daunosamine and D-ristosamine by silica gel promoted intramolecular conjugate addition of trichloroacetimidates obtained from osmundalactone and its epimer. Eur J Org Chem 2206-2211. doi: 10.1002/ejoc.200901402
    • (2010) Eur J Org Chem , pp. 2206-2211
    • Matsushima, Y.1    Kino, J.2
  • 27
    • 64549161157 scopus 로고    scopus 로고
    • Organic reactions on silica in water
    • 10.1021/cr8003955 19072052 10.1021/cr8003955 1:CAS:528:DC%2BD1cXhsFSjtbnF
    • S Minakata M Komatsu 2009 Organic reactions on silica in water Chem Rev 109 711 724 10.1021/cr8003955 19072052 10.1021/cr8003955 1:CAS:528: DC%2BD1cXhsFSjtbnF
    • (2009) Chem Rev , vol.109 , pp. 711-724
    • Minakata, S.1    Komatsu, M.2
  • 28
    • 2542462020 scopus 로고    scopus 로고
    • An efficient synthesis of 2-amino alcohols by silica gel catalysed opening of epoxide rings by amines
    • 10.1039/b400588k 15105916 10.1039/b400588k 1:CAS:528:DC%2BD2cXjsVWjtbk%3D
    • AK Chakraborti S Rudrawar A Kondaskar 2004 An efficient synthesis of 2-amino alcohols by silica gel catalysed opening of epoxide rings by amines Org Biomol Chem 2 1277 1280 10.1039/b400588k 15105916 10.1039/b400588k 1:CAS:528:DC%2BD2cXjsVWjtbk%3D
    • (2004) Org Biomol Chem , vol.2 , pp. 1277-1280
    • Chakraborti, A.K.1    Rudrawar, S.2    Kondaskar, A.3
  • 29
    • 78650175991 scopus 로고    scopus 로고
    • Wells-Dawson heteropolyacid supported on silica: A highly efficient catalyst for synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles
    • doi: 10.1007/s11030-009-9197-x
    • Karimi AR, Alimohammadi Z, Amini MM (2009) Wells-Dawson heteropolyacid supported on silica: a highly efficient catalyst for synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles. Mol Divers doi: 10.1007/s11030-009-9197-x
    • (2009) Mol Divers
    • Karimi, A.R.1    Alimohammadi, Z.2    Amini, M.M.3
  • 30
    • 33947361600 scopus 로고    scopus 로고
    • An efficient regiospecific synthesis of highly functionalised novel dihydro-pyrimido [4,5-d]pyrimidine derivatives by a three-component one-pot condensation under solvent-free conditions
    • doi: 10.1055/s-2007-970739
    • Prajapati D, Borah KJ, Gohain M (2007) An efficient regiospecific synthesis of highly functionalised novel dihydro-pyrimido [4,5-d]pyrimidine derivatives by a three-component one-pot condensation under solvent-free conditions. Synlett 595-598. doi: 10.1055/s-2007-970739
    • (2007) Synlett , pp. 595-598
    • Prajapati, D.1    Borah, K.J.2    Gohain, M.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.