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Volumn 34, Issue 20, 2004, Pages 3773-3783

The facile route to stereodefined alkenyl-substituted pyrimidines

Author keywords

Chloropyrimidines; Organoboronic acid; Suzuki Miyaura cross coupling reaction

Indexed keywords

2,4 DICHLOROPYRIMIDINE; 2,4,6 TRICHLOROPYRIMIDINE; ALKENYL GROUP; BORONIC ACID DERIVATIVE; ORGANOBORON DERIVATIVE; PALLADIUM; PYRIMIDINE DERIVATIVE; SOLVENT; TETRAHYDROFURAN; TOLUENE; UNCLASSIFIED DRUG;

EID: 7444267909     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-200032495     Document Type: Article
Times cited : (7)

References (32)
  • 1
    • 0013263025 scopus 로고
    • Synthesis & antifungal & antibacterial activities of some 2-amino-4,6-substituted-pyrimidines &4-styryl-6,7-pyranoocoumarins
    • (a) Ahluvwalia, V.K.; Kaila, N.; Bala, S. Synthesis & antifungal & antibacterial activities of some 2-amino-4,6-substituted-pyrimidines &4-styryl-6,7-pyranoocoumarins. Indina J. Chem., sect. B 1987, 26, 700-702;
    • (1987) Indina J. Chem., Sect. B , vol.26 , pp. 700-702
    • Ahluvwalia, V.K.1    Kaila, N.2    Bala, S.3
  • 2
    • 0042175778 scopus 로고
    • A facile one-pot conversion of chalcones to pyrimidine derivatives and their antimicrobial and antifungal activities
    • (b) El-hadhash, M.A.; Mahmoud, M.R.; Madboli, S.A. A facile one-pot conversion of chalcones to pyrimidine derivatives and their antimicrobial and antifungal activities. India J. Chem., sect. B 1993, 32, 449-452.
    • (1993) India J. Chem., Sect. B , vol.32 , pp. 449-452
    • El-Hadhash, M.A.1    Mahmoud, M.R.2    Madboli, S.A.3
  • 4
    • 0001450616 scopus 로고    scopus 로고
    • Model systems for flavoenzyme activity. Regulation of flavin recognition via modulation of receptor hydrogen-bond donor-acceptor properties
    • (a) Deans, R.; Cooke, G.; Rotello, V.M. Model systems for flavoenzyme activity. Regulation of flavin recognition via modulation of receptor hydrogen-bond donor-acceptor properties. J. Org. Chem. 1997, 62, 836-839;
    • (1997) J. Org. Chem. , vol.62 , pp. 836-839
    • Deans, R.1    Cooke, G.2    Rotello, V.M.3
  • 5
    • 0000002354 scopus 로고    scopus 로고
    • Hydrogen-bonded complexes of diaminopyridines and diaminotriazines: Opposite effect of acylation on complex stabilities
    • (b) Beijer, F.H.; Siljesma, R.P.; Vekmans, J.A.J.M.; Beijer, E.W.; Kooijiman, H.; Spek, A.L. Hydrogen-bonded complexes of diaminopyridines and diaminotriazines: opposite effect of acylation on complex stabilities. J. Org. Chem. 1996, 61, 6371-6800;
    • (1996) J. Org. Chem. , vol.61 , pp. 6371-6800
    • Beijer, F.H.1    Siljesma, R.P.2    Vekmans, J.A.J.M.3    Beijer, E.W.4    Kooijiman, H.5    Spek, A.L.6
  • 7
    • 0037323452 scopus 로고    scopus 로고
    • A novel frustrated phase produced by a binary system of non-symmetric dimeric liquid crystals
    • Yoshizawa, A.; Yamamoto, K.; Dewa, H.; Nishiyama, I.; Yamamoto, J.; Yamamoto, H.J. A novel frustrated phase produced by a binary system of non-symmetric dimeric liquid crystals. Mater. Chem. 2003,13, 172-174.
    • (2003) Mater. Chem. , vol.13 , pp. 172-174
    • Yoshizawa, A.1    Yamamoto, K.2    Dewa, H.3    Nishiyama, I.4    Yamamoto, J.5    Yamamoto, H.J.6
  • 8
    • 37049158314 scopus 로고
    • Substitution reactions of pyrimidine and its 2- and 4-phenyl derivatives
    • (a) Rayner, L. Substitution reactions of pyrimidine and its 2- and 4-phenyl derivatives. J. Chem. Soc. 1951, 2323-2327;
    • (1951) J. Chem. Soc. , pp. 2323-2327
    • Rayner, L.1
  • 9
    • 0013560123 scopus 로고
    • Synthesis of 2-alkenylpyrimidines via 2-alkenyl-1,4,5,6- tetrahydropyrimidines
    • (b) Richard, G.P. Synthesis of 2-alkenylpyrimidines via 2-alkenyl-1,4,5,6-tetrahydropyrimidines. Heterocycles 1988, 27 (3), 1867-1872;
    • (1988) Heterocycles , vol.27 , Issue.3 , pp. 1867-1872
    • Richard, G.P.1
  • 10
    • 7444243987 scopus 로고    scopus 로고
    • Verfahren zur Herstellung von Verbindungen der Pyrimidinreihe. DE 951990, 1954
    • (c) Matthias, S.; Heinrich, P. Verfahren zur Herstellung von Verbindungen der Pyrimidinreihe. DE 951990, 1954;
    • Matthias, S.1    Heinrich, P.2
  • 11
    • 7444262100 scopus 로고    scopus 로고
    • Production of compounds of the pyrimidine series. US 2778821, 1955
    • (d) Heinrich, P.; Matthias, S.. Production of compounds of the pyrimidine series. US 2778821, 1955;
    • Heinrich, P.1    Matthias, S.2
  • 12
    • 0034234304 scopus 로고    scopus 로고
    • Synthesis of indolylpyrimidines via cross-coupling of indolylboronic acid with chloropyrimidines: Facile synthesis of meridianin D
    • (e) Jiang, B.; Yang, C.G. Synthesis of indolylpyrimidines via cross-coupling of indolylboronic acid with chloropyrimidines: facile synthesis of meridianin D. Heterocycles 2000, 53 (7), 1489-1498;
    • (2000) Heterocycles , vol.53 , Issue.7 , pp. 1489-1498
    • Jiang, B.1    Yang, C.G.2
  • 13
    • 0037036710 scopus 로고    scopus 로고
    • Reaction of α,α-dibromo oxime ethers with Grignard reagents: Alkylative annulation providing a pyrimidine core
    • (f) Hirotada, K.; Kazunari, Y.; Hiroshi, S.; Koichiro, O. Reaction of α,α-dibromo oxime ethers with Grignard reagents: alkylative annulation providing a pyrimidine core. J. Amer. Chem. Soc. 2002, 724 (31), 9032-9033;
    • (2002) J. Amer. Chem. Soc. , vol.724 , Issue.31 , pp. 9032-9033
    • Hirotada, K.1    Kazunari, Y.2    Hiroshi, S.3    Koichiro, O.4
  • 14
    • 0037287387 scopus 로고    scopus 로고
    • Highly efficient synthesis of pyrimidines under microwave-assisted conditions
    • (g) Bagley, M.C.; Hughes, D.D.; Taylor, P.H. Highly efficient synthesis of pyrimidines under microwave-assisted conditions. Syn. Lett. 2003, 2, 259-261;
    • (2003) Syn. Lett. , vol.2 , pp. 259-261
    • Bagley, M.C.1    Hughes, D.D.2    Taylor, P.H.3
  • 15
    • 0038072866 scopus 로고    scopus 로고
    • Helicity-encoded molecular strands: Efficient access by the hydrazone route and structural features
    • (h) Schmitt, J.L.; Stadler, A.M.; Kyritsakas, N.; Lehn, J.M. Helicity-encoded molecular strands: efficient access by the hydrazone route and structural features. Helv. Chim. Acta 2003, 86 (5), 1598-1624;
    • (2003) Helv. Chim. Acta , vol.86 , Issue.5 , pp. 1598-1624
    • Schmitt, J.L.1    Stadler, A.M.2    Kyritsakas, N.3    Lehn, J.M.4
  • 16
    • 0037011739 scopus 로고    scopus 로고
    • Cross-coupling reactions with boronic acids in water catalysed by oxime-derived palladacycles
    • (i) Botella, L.; Najera, C. J. Cross-coupling reactions with boronic acids in water catalysed by oxime-derived palladacycles. Organomet. Chem. 2002, 663 (1-2), 46-57.
    • (2002) Organomet. Chem. , vol.663 , Issue.1-2 , pp. 46-57
    • Botella, L.1    Najera, C.J.2
  • 17
    • 85011216000 scopus 로고
    • Studies on pyrimidine derivaties XX. Synthetic utility of hydroxymethylpyrimidines and related compounds
    • Sakamoto, T.; Tanji, K.; Niitsuma, S.; Ono, T.; Yamanaka, H. Studies on pyrimidine derivaties XX. Synthetic utility of hydroxymethylpyrimidines and related compounds. Chem. Pharm. Bull 1980, 28 (11), 3362-3368.
    • (1980) Chem. Pharm. Bull. , vol.28 , Issue.11 , pp. 3362-3368
    • Sakamoto, T.1    Tanji, K.2    Niitsuma, S.3    Ono, T.4    Yamanaka, H.5
  • 18
    • 0000569934 scopus 로고
    • Synthesis of pyrimidinyl triflates and Palladium-catalyzed coupling with organotion and organozic reagents
    • (a) Sandosham, J.; Undheim, K. Synthesis of pyrimidinyl triflates and Palladium-catalyzed coupling with organotion and organozic reagents. Heterocycle 1994, 37, 501-514;
    • (1994) Heterocycle , vol.37 , pp. 501-514
    • Sandosham, J.1    Undheim, K.2
  • 19
    • 0027954863 scopus 로고
    • Stannylation in the electrophilic 2- and 4/6-pyrimidine position and the use of stannylpyrimidines in coupling and tin-lithium exchange reactions
    • (b) Sandosham, J.; Undheim, K. Stannylation in the electrophilic 2- and 4/6-pyrimidine position and the use of stannylpyrimidines in coupling and tin-lithium exchange reactions. Tetrahedron 1994, 50 (1), 275-284.
    • (1994) Tetrahedron , vol.50 , Issue.1 , pp. 275-284
    • Sandosham, J.1    Undheim, K.2
  • 20
    • 0011791606 scopus 로고    scopus 로고
    • Ethenylation and alkenylation in palladium-catalyzed carbosubstitution in heteroazines
    • Mangalagiu, I.; Benneche, T.; Undheim, K. Ethenylation and alkenylation in palladium-catalyzed carbosubstitution in heteroazines. Acta. Chem. Scand. 1996, 50, 914-917.
    • (1996) Acta. Chem. Scand. , vol.50 , pp. 914-917
    • Mangalagiu, I.1    Benneche, T.2    Undheim, K.3
  • 22
    • 0000276913 scopus 로고
    • 1,3,2-Benzodioxaborole, a convenient monofunctional hydroborating agent. Simple new synthesis of alkaneboronic esters and acids from olefins via hydroboration
    • (b) Brown, H.C.; Gupta, S.K. J. 1,3,2-Benzodioxaborole, a convenient monofunctional hydroborating agent. Simple new synthesis of alkaneboronic esters and acids from olefins via hydroboration. Am. Chem. Soc. 1971, 93, 1816-1818;
    • (1971) Am. Chem. Soc. , vol.93 , pp. 1816-1818
    • Brown, H.C.1    Gupta, S.K.J.2
  • 23
    • 0001695570 scopus 로고
    • Catecholborane (1,3,2-benzodioxaorole) as a new, general monohydroboration reagent for alkynes. Convenient synthesis of alkeneboronic esters and acids from alkynes via hydroboration
    • (c) Brown, H.C.; Gupta, S.K. J. Catecholborane (1,3,2-benzodioxaorole) as a new, general monohydroboration reagent for alkynes. Convenient synthesis of alkeneboronic esters and acids from alkynes via hydroboration. Am. Chem. Soc. 1972, 94, 4370-4371;
    • (1972) Am. Chem. Soc. , vol.94 , pp. 4370-4371
    • Brown, H.C.1    Gupta, S.K.J.2
  • 24
    • 0000925785 scopus 로고
    • A new hydroboration reagent
    • (d) Lane, C.F. A new hydroboration reagent. Tetrahedron 1976, 52, 981-990.
    • (1976) Tetrahedron , vol.52 , pp. 981-990
    • Lane, C.F.1
  • 25
    • 2042507954 scopus 로고
    • Palladium-catalyzed cross-coupling reactions of organoboron compounds
    • (a) Miyaura, N.; Suzuki, A. Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chem. Rev. 1995, 95, 2457-2483;
    • (1995) Chem. Rev. , vol.795 , pp. 2457-2483
    • Miyaura, N.1    Suzuki, A.2
  • 26
    • 0346786657 scopus 로고    scopus 로고
    • Recent advances in the cross-coupling reactions of organoboron derivatives with organic electrophiles
    • (b) Suzuki, A.J. Recent advances in the cross-coupling reactions of organoboron derivatives with organic electrophiles. Organomet. Chem. 1999, 576, 147-168;
    • (1999) Organomet. Chem. , vol.576 , pp. 147-168
    • Suzuki, A.J.1
  • 27
    • 0002681507 scopus 로고
    • Palladium-catalyzed reaction of 1-alkenylboronates with vinylic halides: (1Z, 3E)-1-phenyl-1,3-octadiene
    • (c) Miyaura, N.; Suzuki, A. Palladium-catalyzed reaction of 1-alkenylboronates with vinylic halides: (1Z, 3E)-1-phenyl-1,3-octadiene. Org. Synth. 1990, 68, 130;
    • (1990) Org. Synth. , vol.68 , pp. 130
    • Miyaura, N.1    Suzuki, A.2
  • 28
    • 33751385493 scopus 로고
    • Palladium-catalyzed cross-coupling reaction of organoboron compounds with organic triflates
    • (d) Oh-e, T.; Miyaura, N.; Suzuki, A. Palladium-catalyzed cross-coupling reaction of organoboron compounds with organic triflates. J. Org. Chem. 1993, 58, 2201;
    • (1993) J. Org. Chem. , vol.58 , pp. 2201
    • Oh-E, T.1    Miyaura, N.2    Suzuki, A.3
  • 29
    • 0001683558 scopus 로고
    • A stereospecific synthesis of conjugated (E,Z)- and (E,E)-alkadienes by the palladium-catalyzed reaction of (E)-1-alkenylboronic acids and 1-alkenyl iodides
    • (e) Cassani, G.; Nassardo, P. A stereospecific synthesis of conjugated (E,Z)- and (E,E)-alkadienes by the palladium-catalyzed reaction of (E)-1-alkenylboronic acids and 1-alkenyl iodides. Tetrahedron Lett. 1982, 24 (24), 2513.
    • (1982) Tetrahedron Lett. , vol.24 , Issue.24 , pp. 2513
    • Cassani, G.1    Nassardo, P.2
  • 30
    • 0037195743 scopus 로고    scopus 로고
    • Suzuki-Miyaura cross-coupling reactions of potassium alkenyltrifluoroborates
    • Molander, G.A.; Bernardi, C.R. Suzuki-Miyaura cross-coupling reactions of potassium alkenyltrifluoroborates. J. Org. Chem. 2002, 67 (24), 8424-8429.
    • (2002) J. Org. Chem. , vol.67 , Issue.24 , pp. 8424-8429
    • Molander, G.A.1    Bernardi, C.R.2
  • 31
    • 43949175662 scopus 로고
    • Regioselective substitution in triflyloxypyrimidines and chloropyrimidines using zinc and tin reagents
    • Sandosham, J.; Undheim, K.; Rise, F. Regioselective substitution in triflyloxypyrimidines and chloropyrimidines using zinc and tin reagents. Heterocycle 1993, 35, 235.
    • (1993) Heterocycle , vol.35 , pp. 235
    • Sandosham, J.1    Undheim, K.2    Rise, F.3
  • 32
    • 0002859768 scopus 로고
    • Regiochemistry in Pd-catalysed organotin reaction with halopyrimidines
    • Solberg, J.; Undheim, K. Regiochemistry in Pd-catalysed organotin reaction with halopyrimidines. Acta. Chem. Scand. 1989, 43, 62-68.
    • (1989) Acta. Chem. Scand. , vol.43 , pp. 62-68
    • Solberg, J.1    Undheim, K.2


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