Synthetic strategies to prepare 2-alkyl, 2-aryl and 2-acetylenyl substituted 4,6-diamino-1,3,5-triazines

Strategies for introduction of malonyl, aryl or alkynyl substituents onto a triazine ring are described. We have developed synthetic protocols to generate 2-alkyl, 2-aryl and 2-acetylenyl substituted 4,6-diamino-1,3,5-triazines from the corresponding 2-chloro compound.

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Published inTetrahedron letters Vol. 47; no. 33; pp. 5973 - 5975
Main Authors Montalbetti, Christian A.G.N., Coulter, Thomas S., Uddin, Muhammed K., Reignier, Serge G., Magaraci, Filippo, Grånäs, Charlotta, Krog-Jensen, Christian, Felding, Jakob
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 14.08.2006
Elsevier
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Abstract Strategies for introduction of malonyl, aryl or alkynyl substituents onto a triazine ring are described. We have developed synthetic protocols to generate 2-alkyl, 2-aryl and 2-acetylenyl substituted 4,6-diamino-1,3,5-triazines from the corresponding 2-chloro compound.
AbstractList Strategies for introduction of malonyl, aryl or alkynyl substituents onto a triazine ring are described. We have developed synthetic protocols to generate 2-alkyl, 2-aryl and 2-acetylenyl substituted 4,6-diamino-1,3,5-triazines from the corresponding 2-chloro compound.
We have developed synthetic protocols to generate 2-alkyl, 2-aryl and 2-acetylenyl substituted 4,6-diamino-1,3,5-triazines from the corresponding 2-chloro compound. (c) 2006 Elsevier Ltd. All rights reserved.
Author Krog-Jensen, Christian
Felding, Jakob
Magaraci, Filippo
Coulter, Thomas S.
Uddin, Muhammed K.
Montalbetti, Christian A.G.N.
Reignier, Serge G.
Grånäs, Charlotta
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Cites_doi 10.1021/jm049372z
10.1021/jm0495374
10.1021/cc049965v
10.1177/108705710429989
10.1021/jm020291h
10.1021/ja026720i
10.1021/jm980222w
10.1016/S0040-4020(01)00119-3
10.1016/S0040-4020(98)00138-0
10.1016/S0040-4039(00)91094-3
10.1177/1087057104269989
10.1016/S0040-4039(99)01737-2
10.1021/jm960148m
10.1021/cr00039a007
10.1016/S0040-4020(98)00134-3
10.1016/S0040-4020(00)00925-X
10.1016/S1535-6108(03)00303-9
10.1016/S0968-0896(98)00266-1
10.1016/S0040-4020(01)01230-3
10.2116/analsci.20.227
10.1002/hlca.19500330536
10.1007/BF00961962
10.1016/0960-894X(96)00145-X
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Issue 33
Keywords Triazine
Sonogashira
PI3 Kinase pathway inhibitors
Nucleophilic substitution
Suzuki
FOXO1 Translocation
PALLADIUM
TRIAZINE LIBRARY
TUMOR-CELLS
CROSS-COUPLING REACTIONS
ORTHOGONAL SYNTHESIS
FOXO1 translocation
nucleophilic substitution
triazine
PI3 kinase pathway inhibitors
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ANTAGONISTS
CHLORIDE
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References Kau, Schroeder, Ramaswamy, Wojciechowski, Zhao, Roberts, Clardy, Sellers, Silver (bib2) 2003; 4
Gustafson, Baldino, O’Donnel, Sheldon, Tarsa, Verni, Coffen, Johnson, Zhang, Fantauzzi, Hocker, Yager (bib5) 1998; 54
Menicagli, Samaritani, Zucchelli, Menicagli, Samaritani, Signore, Vaglini, Dalla Via (bib14) 2000; 56
Sonogashira, Tohda, Hagihara (bib12) 1975; 50
Hirt, Nidecker, Berchtold, Schönholzer, Leroux, van Keulen, Daliers, Pommery, Henichart, Arvanitis, Gilligan, Chorvat, Cheeseman, Christos, Bakthavatchalam, Beck, Cocuzza, Hobbs, Wilde, Arnold, Chidester, Curry, He, Hollis, Klaczkiewicz, Krenitsky, Rescinito, Scholfield, Culp, De Souza, Fitzgerald, Grigoriadis, Tam, Wong, Huang, Shen (bib8) 1950; 33
Miyaura, Suzuki (bib10) 1995; 95
Xia, Mirzai, Chackalamannil, Czarniecki, Wang, Clemmons, Ahn, Boykow (bib7) 1996; 6
Henke, Consler, Go, Hale, Hohman, Jones, Lu, Moore, Moore, Orband-Miller, Robinett, Shearin, Spearing, Stewart, Turnbull, Weaver, Williams, Wisely, Lambert (bib4) 2002; 45
Menicagli, Samaritani, Gori, Samaritani, Menicagli (bib13) 1999; 40
Khersonsky, Chang (bib6) 2004; 6
Lundholt, Linde, Loechel, Pedersen, Møller, Præstegaard, Mikkelsen, Scudder, Bjørn, Heide, Arkhammar, Terry, Nielsen (bib3) 2005; 10
Cooke, de Cremier, Rotello, Tarbit, Vanderstraeten (bib11) 2001; 57
Shastin, Rakitin, Godovikova, Strelenko, Dubovitskii, Khmel’nitskii (bib9) 1988; 37
Coon, Ball, Pound, Ap, Hollenback, White, Tulinsky, Bonham, Morrison, Finney, Singer, Moon, Jacobson, Khersonsky, Luzung, Walsh, Xiong, Lee, Parikh, Lam, Kang, Rosania, Schier, Chang, Baindur, Chadha, Brandt, Asgari, Patch, Schalk-HiHi, Carver, Petrounia, Baumann, Ott, Manthey, Springer, Player, Whitten, Xie, Erickson, Webb, De Souza, Grigoriadis, McCarthy, Tanabe, Kawata (bib1) 2003; 2
SHASTIN AV (WOS:000239289800031.19) 1988; 6
Leroux, F (WOS:000079460700009) 1999; 7
Samaritani, S (WOS:000174339600016) 2002; 58
Khersonsky, SM (WOS:000222671900006) 2004; 6
Moon, HS (WOS:000178317100024) 2002; 124
Johnson, CR (WOS:000072787200012) 1998; 54
Menicagli, R (WOS:000223699600004) 2004; 47
Whitten, JP (WOS:A1996VP24700002) 1996; 39
HIRT, R (WOS:A1950UC44100035) 1950; 33
Coon, M (WOS:000186054800015) 2003; 2
Baindur, N (WOS:000227749300010) 2005; 48
Arvanitis, AG (WOS:000079143000005) 1999; 42
Tanabe, A (WOS:000188289700042) 2004; 20
Cooke, G (WOS:000167884400015) 2001; 57
Kau, TR (WOS:000187583200009) 2003; 4
MIYAURA, N (WOS:A1995TD89200007) 1995; 95
Henke, BR (WOS:000179632500011) 2002; 45
Menicagli, R (WOS:000083545800026) 1999; 40
Menicagli, R (WOS:000165485500022) 2000; 56
Xia, Y (WOS:A1996UG18000040) 1996; 6
Lundholt, BK (WOS:000227050000003) 2005; 10
Gustafson, GR (WOS:000072787200008) 1998; 54
SHASTIN, AV (WOS:A1988T981400035) 1988; 37
SONOGASHIRA K (WOS:000239289800031.21) 1975; 50
Menicagli (10.1016/j.tetlet.2006.06.045_bib14_1) 2000; 56
Samaritani (10.1016/j.tetlet.2006.06.045_bib13_2) 2002; 58
Moon (10.1016/j.tetlet.2006.06.045_bib1b) 2002; 124
Hirt (10.1016/j.tetlet.2006.06.045_bib8_1) 1950; 33
Arvanitis (10.1016/j.tetlet.2006.06.045_bib8_3) 1999; 42
Khersonsky (10.1016/j.tetlet.2006.06.045_bib6) 2004; 6
Baindur (10.1016/j.tetlet.2006.06.045_bib1c) 2005; 48
Lundholt (10.1016/j.tetlet.2006.06.045_bib3) 2005; 10
Menicagli (10.1016/j.tetlet.2006.06.045_bib14_2) 2004; 47
Cooke (10.1016/j.tetlet.2006.06.045_bib11) 2001; 57
(10.1016/j.tetlet.2006.06.045_bib9_2) 1988; 6
Tanabe (10.1016/j.tetlet.2006.06.045_bib1_5) 2004; 20
Kau (10.1016/j.tetlet.2006.06.045_bib2) 2003; 4
Johnson (10.1016/j.tetlet.2006.06.045_bib5_2) 1998; 54
Coon (10.1016/j.tetlet.2006.06.045_bib1_1) 2003; 2
Gustafson (10.1016/j.tetlet.2006.06.045_bib5_1) 1998; 54
Henke (10.1016/j.tetlet.2006.06.045_bib4) 2002; 45
Menicagli (10.1016/j.tetlet.2006.06.045_bib13_1) 1999; 40
Whitten (10.1016/j.tetlet.2006.06.045_bib1_4) 2002; 39
Miyaura (10.1016/j.tetlet.2006.06.045_bib10) 1995; 95
Xia (10.1016/j.tetlet.2006.06.045_bib7) 1996; 6
Shastin (10.1016/j.tetlet.2006.06.045_bib9_1) 1988; 37
Sonogashira (10.1016/j.tetlet.2006.06.045_bib12) 1975; 50
Leroux (10.1016/j.tetlet.2006.06.045_bib8_2) 1999; 7
References_xml – volume: 50
  start-page: 4467
  year: 1975
  end-page: 4470
  ident: bib12
  publication-title: Tetrahedron Lett.
  contributor:
    fullname: Hagihara
– volume: 45
  start-page: 5492
  year: 2002
  end-page: 5505
  ident: bib4
  publication-title: J. Med. Chem.
  contributor:
    fullname: Lambert
– volume: 10
  start-page: 20
  year: 2005
  end-page: 29
  ident: bib3
  publication-title: J. Biomol. Screen
  contributor:
    fullname: Nielsen
– volume: 95
  start-page: 2457
  year: 1995
  ident: bib10
  publication-title: Chem. Rev.
  contributor:
    fullname: Suzuki
– volume: 2
  start-page: 1067
  year: 2003
  end-page: 1078
  ident: bib1
  publication-title: Mol. Cancer Ther.
  contributor:
    fullname: Kawata
– volume: 4
  start-page: 463
  year: 2003
  end-page: 476
  ident: bib2
  publication-title: Cancer Cell
  contributor:
    fullname: Silver
– volume: 6
  start-page: 919
  year: 1996
  end-page: 922
  ident: bib7
  publication-title: Bioorg. Med. Chem. Lett.
  contributor:
    fullname: Boykow
– volume: 56
  start-page: 9705
  year: 2000
  end-page: 9712
  ident: bib14
  publication-title: Tetrahedron
  contributor:
    fullname: Dalla Via
– volume: 40
  start-page: 8419
  year: 1999
  end-page: 8422
  ident: bib13
  publication-title: Tetrahedron Lett.
  contributor:
    fullname: Menicagli
– volume: 37
  start-page: 1282
  year: 1988
  end-page: 1448
  ident: bib9
  publication-title: Bull. Acad. Sci. USSR Div. Chem. Sci.
  contributor:
    fullname: Khmel’nitskii
– volume: 6
  start-page: 474
  year: 2004
  end-page: 477
  ident: bib6
  publication-title: J. Comb. Chem.
  contributor:
    fullname: Chang
– volume: 54
  start-page: 4051
  year: 1998
  end-page: 4065
  ident: bib5
  publication-title: Tetrahedron
  contributor:
    fullname: Yager
– volume: 57
  start-page: 2787
  year: 2001
  end-page: 2789
  ident: bib11
  publication-title: Tetrahedron
  contributor:
    fullname: Vanderstraeten
– volume: 33
  start-page: 1365
  year: 1950
  end-page: 1368
  ident: bib8
  publication-title: Helv. Chim. Acta
  contributor:
    fullname: Shen
– volume: 54
  start-page: 4097
  year: 1998
  ident: WOS:000072787200012
  article-title: Libraries of N-alkylaminoheterocycles from nucleophilic aromatic substitution with purification by solid supported liquid extraction
  publication-title: TETRAHEDRON
  contributor:
    fullname: Johnson, CR
– volume: 39
  start-page: 4354
  year: 1996
  ident: WOS:A1996VP24700002
  article-title: Rapid microscale synthesis, a new method for lead optimization using robotics and solution phase chemistry: Application to the synthesis and optimization of corticotropin-releasing factor(1) receptor antagonists
  publication-title: JOURNAL OF MEDICINAL CHEMISTRY
  contributor:
    fullname: Whitten, JP
– volume: 4
  start-page: 463
  year: 2003
  ident: WOS:000187583200009
  article-title: A chemical genetic screen identifies inhibitors of regulated nuclear export of a Forkhead transcription factor in PTEN-deficient tumor cells
  publication-title: CANCER CELL
  contributor:
    fullname: Kau, TR
– volume: 37
  start-page: 1282
  year: 1988
  ident: WOS:A1988T981400035
  article-title: REACTION OF SILYL ENOL ETHERS WITH CYANOGEN CHLORIDE
  publication-title: BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE
  contributor:
    fullname: SHASTIN, AV
– volume: 40
  start-page: 8419
  year: 1999
  ident: WOS:000083545800026
  article-title: 2-(alk-1 '-ynyl)-4,6-dimethoxy-1,3,5-triazines via Pd-mediated alkynylation of 2-chloro-4,6-dimethoxy-1,3,5-triazine
  publication-title: TETRAHEDRON LETTERS
  contributor:
    fullname: Menicagli, R
– volume: 33
  start-page: 1365
  year: 1950
  ident: WOS:A1950UC44100035
  article-title: SYNTHESEN MIT CYANURSAURECHLORID
  publication-title: HELVETICA CHIMICA ACTA
  contributor:
    fullname: HIRT, R
– volume: 2
  start-page: 1067
  year: 2003
  ident: WOS:000186054800015
  article-title: Inhibition of lysophosphatidic acid acyltransferase disrupts proliferative and survival signals in normal cells and induces apoptosis of tumor cells
  publication-title: MOLECULAR CANCER THERAPEUTICS
  contributor:
    fullname: Coon, M
– volume: 20
  start-page: 227
  year: 2004
  ident: WOS:000188289700042
  article-title: Determination of triazine pesticides and related compounds in environmental water by liquid chromatography-mass spectrometry
  publication-title: ANALYTICAL SCIENCES
  contributor:
    fullname: Tanabe, A
– volume: 6
  start-page: 1447
  year: 1988
  ident: WOS:000239289800031.19
  publication-title: IAN SSSR KH
  contributor:
    fullname: SHASTIN AV
– volume: 48
  start-page: 1717
  year: 2005
  ident: WOS:000227749300010
  article-title: 2-Hydroxy-4,6-diamino-[1,3,5]triazines: A novel class of VEGF-R2 (KDR) tyrosine kinase inhibitors
  publication-title: JOURNAL OF MEDICINAL CHEMISTRY
  doi: 10.1021/jm049372z
  contributor:
    fullname: Baindur, N
– volume: 57
  start-page: 2787
  year: 2001
  ident: WOS:000167884400015
  article-title: Synthesis of 6-aryl-2,4-diamino-pyrimidines and triazines using palladium catalysed Suzuki cross-coupling reactions
  publication-title: TETRAHEDRON
  contributor:
    fullname: Cooke, G
– volume: 47
  start-page: 4649
  year: 2004
  ident: WOS:000223699600004
  article-title: In vitro cytotoxic activities of 2-alkyl-4,6-diheteroalkyl-1,3,5-triazines: New molecules in anticancer research
  publication-title: JOURNAL OF MEDICINAL CHEMISTRY
  doi: 10.1021/jm0495374
  contributor:
    fullname: Menicagli, R
– volume: 6
  start-page: 474
  year: 2004
  ident: WOS:000222671900006
  article-title: Safety-catch approach to orthogonal synthesis of a triazine library
  publication-title: JOURNAL OF COMBINATORIAL CHEMISTRY
  doi: 10.1021/cc049965v
  contributor:
    fullname: Khersonsky, SM
– volume: 50
  start-page: 4467
  year: 1975
  ident: WOS:000239289800031.21
  publication-title: TETRAHEDRON LETT
  contributor:
    fullname: SONOGASHIRA K
– volume: 10
  start-page: 20
  year: 2005
  ident: WOS:000227050000003
  article-title: Identification of Akt pathway inhibitors using redistribution screening on the FLIPR and the IN cell 3000 analyzer
  publication-title: JOURNAL OF BIOMOLECULAR SCREENING
  doi: 10.1177/108705710429989
  contributor:
    fullname: Lundholt, BK
– volume: 95
  start-page: 2457
  year: 1995
  ident: WOS:A1995TD89200007
  article-title: PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ORGANOBORON COMPOUNDS
  publication-title: CHEMICAL REVIEWS
  contributor:
    fullname: MIYAURA, N
– volume: 54
  start-page: 4051
  year: 1998
  ident: WOS:000072787200008
  article-title: Incorporation of carbohydrates and peptides into large triazine-based screening libraries using automated parallel synthesis
  publication-title: TETRAHEDRON
  contributor:
    fullname: Gustafson, GR
– volume: 6
  start-page: 919
  year: 1996
  ident: WOS:A1996UG18000040
  article-title: Substituted 1,3,5-triazines as cholesteryl ester transfer protein inhibitors
  publication-title: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
  contributor:
    fullname: Xia, Y
– volume: 7
  start-page: 509
  year: 1999
  ident: WOS:000079460700009
  article-title: Phosphodiesterase 4 inhibitors as airways smooth muscle relaxant agents: Synthesis and biological activities of triazine derivatives
  publication-title: BIOORGANIC & MEDICINAL CHEMISTRY
  contributor:
    fullname: Leroux, F
– volume: 45
  start-page: 5492
  year: 2002
  ident: WOS:000179632500011
  article-title: A new series of estrogen receptor modulators that display selectivity for estrogen receptor beta
  publication-title: JOURNAL OF MEDICINAL CHEMISTRY
  doi: 10.1021/jm020291h
  contributor:
    fullname: Henke, BR
– volume: 42
  start-page: 805
  year: 1999
  ident: WOS:000079143000005
  article-title: Non-peptide corticotropin-releasing hormone antagonists: Syntheses and structure-activity relationships of 2-anilinopyrimidines and -triazines
  publication-title: JOURNAL OF MEDICINAL CHEMISTRY
  contributor:
    fullname: Arvanitis, AG
– volume: 58
  start-page: 1381
  year: 2002
  ident: WOS:000174339600016
  article-title: Palladium on carbon catalyzed cross-coupling between alk-1-ynes and 2-chloro-4,6-dialkoxy-1,3,5-triazines
  publication-title: TETRAHEDRON
  contributor:
    fullname: Samaritani, S
– volume: 124
  start-page: 11608
  year: 2002
  ident: WOS:000178317100024
  article-title: A novel microtubule destabilizing entity from orthogonal synthesis of triazine library and zebrafish embryo screening
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  doi: 10.1021/ja026720i
  contributor:
    fullname: Moon, HS
– volume: 56
  start-page: 9705
  year: 2000
  ident: WOS:000165485500022
  article-title: 2-alkyl-4,6-dialkylamino-1,3,5-triazines via Grignard alkylation of cyanuric chloride: An aged reaction revisited
  publication-title: TETRAHEDRON
  contributor:
    fullname: Menicagli, R
– volume: 42
  start-page: 805
  year: 1999
  ident: 10.1016/j.tetlet.2006.06.045_bib8_3
  publication-title: J. Med. Chem.
  doi: 10.1021/jm980222w
  contributor:
    fullname: Arvanitis
– volume: 45
  start-page: 5492
  year: 2002
  ident: 10.1016/j.tetlet.2006.06.045_bib4
  publication-title: J. Med. Chem.
  doi: 10.1021/jm020291h
  contributor:
    fullname: Henke
– volume: 57
  start-page: 2787
  year: 2001
  ident: 10.1016/j.tetlet.2006.06.045_bib11
  publication-title: Tetrahedron
  doi: 10.1016/S0040-4020(01)00119-3
  contributor:
    fullname: Cooke
– volume: 54
  start-page: 4097
  year: 1998
  ident: 10.1016/j.tetlet.2006.06.045_bib5_2
  publication-title: Tetrahedron
  doi: 10.1016/S0040-4020(98)00138-0
  contributor:
    fullname: Johnson
– volume: 50
  start-page: 4467
  year: 1975
  ident: 10.1016/j.tetlet.2006.06.045_bib12
  publication-title: Tetrahedron Lett.
  doi: 10.1016/S0040-4039(00)91094-3
  contributor:
    fullname: Sonogashira
– volume: 10
  start-page: 20
  year: 2005
  ident: 10.1016/j.tetlet.2006.06.045_bib3
  publication-title: J. Biomol. Screen
  doi: 10.1177/1087057104269989
  contributor:
    fullname: Lundholt
– volume: 124
  start-page: 11608
  year: 2002
  ident: 10.1016/j.tetlet.2006.06.045_bib1b
  publication-title: J. Am. Chem. Soc.
  doi: 10.1021/ja026720i
  contributor:
    fullname: Moon
– volume: 2
  start-page: 1067
  year: 2003
  ident: 10.1016/j.tetlet.2006.06.045_bib1_1
  publication-title: Mol. Cancer Ther.
  contributor:
    fullname: Coon
– volume: 6
  start-page: 1447
  year: 1988
  ident: 10.1016/j.tetlet.2006.06.045_bib9_2
  publication-title: Izv. Akad. Nauk SSSR Ser. Khim.
– volume: 40
  start-page: 8419
  year: 1999
  ident: 10.1016/j.tetlet.2006.06.045_bib13_1
  publication-title: Tetrahedron Lett.
  doi: 10.1016/S0040-4039(99)01737-2
  contributor:
    fullname: Menicagli
– volume: 47
  start-page: 4649
  year: 2004
  ident: 10.1016/j.tetlet.2006.06.045_bib14_2
  publication-title: J. Med. Chem.
  doi: 10.1021/jm0495374
  contributor:
    fullname: Menicagli
– volume: 48
  start-page: 1717
  year: 2005
  ident: 10.1016/j.tetlet.2006.06.045_bib1c
  publication-title: J. Med. Chem.
  doi: 10.1021/jm049372z
  contributor:
    fullname: Baindur
– volume: 39
  start-page: 4354
  year: 2002
  ident: 10.1016/j.tetlet.2006.06.045_bib1_4
  publication-title: J. Med. Chem.
  doi: 10.1021/jm960148m
  contributor:
    fullname: Whitten
– volume: 95
  start-page: 2457
  year: 1995
  ident: 10.1016/j.tetlet.2006.06.045_bib10
  publication-title: Chem. Rev.
  doi: 10.1021/cr00039a007
  contributor:
    fullname: Miyaura
– volume: 54
  start-page: 4051
  year: 1998
  ident: 10.1016/j.tetlet.2006.06.045_bib5_1
  publication-title: Tetrahedron
  doi: 10.1016/S0040-4020(98)00134-3
  contributor:
    fullname: Gustafson
– volume: 56
  start-page: 9705
  year: 2000
  ident: 10.1016/j.tetlet.2006.06.045_bib14_1
  publication-title: Tetrahedron
  doi: 10.1016/S0040-4020(00)00925-X
  contributor:
    fullname: Menicagli
– volume: 4
  start-page: 463
  year: 2003
  ident: 10.1016/j.tetlet.2006.06.045_bib2
  publication-title: Cancer Cell
  doi: 10.1016/S1535-6108(03)00303-9
  contributor:
    fullname: Kau
– volume: 7
  start-page: 509
  year: 1999
  ident: 10.1016/j.tetlet.2006.06.045_bib8_2
  publication-title: Bioorg. Med. Chem.
  doi: 10.1016/S0968-0896(98)00266-1
  contributor:
    fullname: Leroux
– volume: 58
  start-page: 1381
  year: 2002
  ident: 10.1016/j.tetlet.2006.06.045_bib13_2
  publication-title: Tetrahedron
  doi: 10.1016/S0040-4020(01)01230-3
  contributor:
    fullname: Samaritani
– volume: 20
  start-page: 227
  year: 2004
  ident: 10.1016/j.tetlet.2006.06.045_bib1_5
  publication-title: Anal. Sci.
  doi: 10.2116/analsci.20.227
  contributor:
    fullname: Tanabe
– volume: 33
  start-page: 1365
  year: 1950
  ident: 10.1016/j.tetlet.2006.06.045_bib8_1
  publication-title: Helv. Chim. Acta
  doi: 10.1002/hlca.19500330536
  contributor:
    fullname: Hirt
– volume: 6
  start-page: 474
  year: 2004
  ident: 10.1016/j.tetlet.2006.06.045_bib6
  publication-title: J. Comb. Chem.
  doi: 10.1021/cc049965v
  contributor:
    fullname: Khersonsky
– volume: 37
  start-page: 1282
  year: 1988
  ident: 10.1016/j.tetlet.2006.06.045_bib9_1
  publication-title: Bull. Acad. Sci. USSR Div. Chem. Sci.
  doi: 10.1007/BF00961962
  contributor:
    fullname: Shastin
– volume: 6
  start-page: 919
  year: 1996
  ident: 10.1016/j.tetlet.2006.06.045_bib7
  publication-title: Bioorg. Med. Chem. Lett.
  doi: 10.1016/0960-894X(96)00145-X
  contributor:
    fullname: Xia
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Snippet Strategies for introduction of malonyl, aryl or alkynyl substituents onto a triazine ring are described. We have developed synthetic protocols to generate...
We have developed synthetic protocols to generate 2-alkyl, 2-aryl and 2-acetylenyl substituted 4,6-diamino-1,3,5-triazines from the corresponding 2-chloro...
Source Web of Science
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StartPage 5973
SubjectTerms Chemistry
Chemistry, Organic
FOXO1 Translocation
Nucleophilic substitution
Physical Sciences
PI3 Kinase pathway inhibitors
Science & Technology
Sonogashira
Suzuki
Triazine
Title Synthetic strategies to prepare 2-alkyl, 2-aryl and 2-acetylenyl substituted 4,6-diamino-1,3,5-triazines
URI https://dx.doi.org/10.1016/j.tetlet.2006.06.045
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