Phosphonium- and benzotriazolyloxy-mediated bond-forming reactions and their synthetic applications

Synlett

Volumn , Issue 8, 2010, Pages 1143-1169

  Mansour, Tarek S ^a   Bardhan, Sujata ^a   Wan, Zhao Kui ^a  

^a PFIZER INC   (United States)

Author keywords

Aminations; Aryl ethers; Benzotriazoles; Nucleophilic aromatic substitutions; Phosphonium

Indexed keywords

(1H BENZOTRIAZOL 1 YLOXY)TRIAMINOPHOSPHONIUM HEXAFLUOROPHOSPHATE; (1H BENZOTRIAZOL 1 YLOXY)TRIPYRROLIDINYLPHOSPHONIUM HEXAFLUOROPHOSPHATE; (1H BENZOTRIAZOL 1 YLOXY)TRIS(DIMETHYLAMINO)PHOSPHONIUM HEXAFLUOROPHOSPHATE; 1H BENZOTRIAZOL 1 OL; AMIDE; AROMATIC COMPOUND; BENZOTRIAZOLE DERIVATIVE; BENZOTRIAZOLYLOXY; BORONIC ACID DERIVATIVE; BROMOTRIPYRROLIDINYLPHOSPHONIUM HEXAFLUOROPHOSPHATE; CARBON; ETHER DERIVATIVE; HETEROCYCLIC COMPOUND; HYDROGEN PEROXIDE; NITROGEN; OXYGEN; PALLADIUM; PHENOL DERIVATIVE; PHOSPHONIUM DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRIDOTRIAZOL 1 OL; SOLVENT; SULFUR; UNCLASSIFIED DRUG; UREA DERIVATIVE;

ALLYLIC REARRANGEMENT; AMINATION; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; NUCLEOPHILICITY; REVIEW; SUBSTITUTION REACTION; SYNTHESIS;

EID: 77952073508     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1219820     Document Type: Review

References (135)

1. For representative examples, see:, Suhadolnik R J., Nucleosides as Biological Probes Wiley New York 1979
2. Srivastava P C., Robins R K., Meyer R B. Jr., In Chemistry of Nucleosides and Nucleotides Vol. 1 Townsend L B. Plenum New York 1988 113-281
3. Han S, Harris C M., Harris T M., Kim H.-Y H., Kim S J., J. Org. Chem. 1996 61 174
4. Simons C, Wu Q, Htar T T., Curr. Top. Med. Chem. 2005 5 1191; and references cited therein
5. For recent syntheses, see:, Yoon D S., Han Y, Stark T M., Haber J C., Gregg B T., Stankovich S B., Org. Lett. 2004 6 4775; and references cited therein
6. For representative reviews on the pharmaceutical and clinical applications of quinazolinamines, see
7. Fry D W., Kraker A J., McMichael A, Ambroso L A., Nelson J M., Leopold W R., Connors R W., Bridges A J., Science (Washington, DC, U.S.) 1994 265 1093
8. Bridges A J., Chem. Rev. 2001 101 2541
9. Liao [nl]J J.-L, J. Med. Chem. 2007 50 409
10. Corey E J., Grogan M J., Org. Lett. 1999 1 157
11. Weiss M E., Fischer D F., Xin Z.-q, Jautze S, Schweizer W B., Peters R, Angew. Chem. Int. Ed. 2006 45 5694
12. Shen J, Nguyen T T., Goh Y.-P, Ye W, Fu X, Xu J, Tan C.-H, J. Am. Chem. Soc. 2006 128 13692
13. Jautze S, Seiler P, Peters R, Angew. Chem. Int. Ed. 2007 46 1260
14. Fischer D F., Xin Z.-q, Peters R, Angew. Chem. Int. Ed. 2007 46 7704
15. For a few representative examples, see:, Maruenda H, Chenna A, Liem L.-K, Singer B, J. Org. Chem. 1998 63 4385
16. Van Brocklin H F., Lim J K., Coffing S L., Hom D L., Negash K, Ono M Y., Gilmore J L., Bryant I, Riese D J. I. I., J. Med. Chem. 2005 48 7445
17. Wissner A, Floyd M B., Johnson B D., Fraser H, Ingalls C, Nittoli T, Dushin R G., Discafani C, Nilakantan R, Marini J, Ravi M, Cheung K, Tan X, Musto S, Annable T, Siegel M M., Loganzo F, J. Med. Chem. 2005 48 7560
18. Mishani E, Abourbeh G, Jacobson O, Dissoki S, Daniel R B., Rozen Y, Shaul M, Levitzki A, J. Med. Chem. 2005 48 5337
19. Domarkas J, Dudouit F, Williams C, Qiyu Q, Banerjee R, Brahimi F, Jean-Claude B J., J. Med. Chem. 2006 49 3544
20. For general Buchwald-Hartwig aminations, see:, Wagaw S, Buchwald S L., J. Org. Chem. 1996 61 7240
21. Old D W., Wolfe J P., Buchwald S L., J. Am. Chem. Soc. 1998 120 9722
22. Wolfe J P., Wagaw S, Marcoux J.-F, Buchwald S L., Acc. Chem. Res. 1998 31 805
23. Hartwig J F., Angew. Chem. Int. Ed. 1998 37 2046
24. Hartwig J F., Acc. Chem. Res. 1998 31 852
25. Castro B, Dormoy J R., Evin G, Selve C, Tetrahedron Lett. 1975 16 1219
26. Coste J, Frrot E, Jouin P, J. Org. Chem. 1994 59 2437
27. Campagne [nl]J.-M, Coste J, Jouin P, J. Org. Chem. 1995 60 5214
28. Kim M H., Patel D V., Tetrahedron Lett. 1994 35 5603
29. Coste J, Campagne J.-M, Tetrahedron Lett. 1995 36 4253
30. Castro B, Chapleur Y, Gross B, Selve C, Tetrahedron Lett. 1972 13 5001
31. Castro B, Selve C, Tetrahedron Lett. 1973 14 4459
32. Downie I M., Heaney H, Kemp G, Tetrahedron Lett. 1988 44 2619
33. Wan Z.-K, Binnun E, Wilson D, Lee J, Org. Lett. 2005 7 5877
34. Wan Z.-K, Wacharasindhu S, Binnun E, Mansour T, Org. Lett. 2006 8 2425
35. Wan Z.-K, Wacharasindhu S, Levins C, Lin M, Tabei K, Mansour T S., J. Org. Chem. 2007 72 10194
36. De Napoli L, Messere A, Montesarchio D, Piccialli G, Santacroce C, Nucleosides Nucleotides 1991 10 1719
37. De Napoli L, Messere A, Montesarchio D, Piccialli G, Santacroce C, Varra M, J. Chem. Soc., Perkin Trans. 1 1994 923
38. Appel R, Angew. Chem. Int. Ed. Engl. 1975 14 801
39. Vliz E A., Beal P A., Tetrahedron Lett. 2000 41 1695
40. Vliz E A., Beal P A., J. Org. Chem. 2001 66 8592
41. Hans J J., Deriver R W., Burke S D., J. Org. Chem. 1999 64 1430
42. Bae S, Lakshman M K., J. Org. Chem. 2008 73 1311
43. Lin X, Robins M J., Org. Lett. 2000 2 3497
44. Janeba Z, Lin X, Robins M J., Nucleosides, Nucleotides Nucleic Acids 2004 23 137
45. Zhong M, Nowak I, Cannon J F., Robins M J., J. Org. Chem. 2006 71 4216
46. Zhong M, Nowak I, Robins M J., Org. Lett. 2005 7 4601
47. Wan Z.-K, Lee J, Hotchandani R, Moretto A, Binnun E, Wilson D P., Kirincich S J., Follows B C., Ipek M, Xu W, Joseph-McCarthy D, Zhang Y.-L, Tam M, Erbe D V., Tobin J F., Li W, Tam S Y., Mansour T S., Wu J, ChemMedChem 2008 3 1525; and references cited therein
48. For representative examples, see
49. Nair V, Richardson S G., J. Org. Chem. 1980 45 3969
50. Liu J, Janeba Z, Robins M J., Org. Lett. 2004 6 2917
51. Lakshman M K., [nl]J. Organomet. Chem. 2002 653 234
52. Hocek M, Eur. J. Org. Chem. 2003 245
53. Robins M J., Basom G L., Can. J. Chem. 1973 51 3161
54. Lee H, Luna E, Hinz M, Stezowski J J., Kiselyov A S., Harvey R G., J. Org. Chem. 1995 60 5604
55. Maruenda H, Chenna A, Liem L.-K, Singer B, [nl]J. Org. Chem. 1998 63 4385
56. Lakshman M K., Sayer J M., Jerina D M., J. Am. Chem. Soc. 1991 113 6589
57. Kim S J., Harris C M., Jung K.-Y, Koreeda M, Harris T M., Tetrahedron Lett. 1991 32 6073
58. Lakshman M K., Keeler J C., Hilmer J H., Martin [nl]J Q., J. Am. Chem. Soc. 1999 121 6090
59. De Riccardis F, Bonala R R., Johnson F, J. Am. Chem. Soc. 1999 121 10453
60. Elmquist C E., Stover J S., Wang Z, Rizzo [nl]C J., J. Am. Chem. Soc. 2004 126 11190
61. Dai Q, Ran C, Harvey R G., Org. Lett. 2005 7 999
62. Sung W L., J. Org. Chem. 1982 47 3623
63. Mansour T S., Evans C A., Siddiqui M A., Charron M, Zacharie B, Nguyen-Ba N, Lee N, Korba B, Nucleosides Nucleotides 1997 16 993
64. Harvey R G., Polycyclic Aromatic Hydrocarbons: Chemistry and Carcinogenicity Cambridge University Cambridge / UK 1991
65. Glatt H, Seidel A, Harvey [nl]R G., Coughtrie M W. H., Mutagenesis 1994 9 553
66. Seela F, Herdering W, Kehne A, Helv. Chim. Acta 1987 70 1649
67. Printz M, Richert C, Chem. Eur. J. 2009 15 3390
68. Wu W, Stupi B P., Litosh V A., Mansouri D, Farley D, Morris S, Metzker S, Metzker M L., Nucleic Acids Res. 2007 35 6339
69. Sakkar S, Perlstein E O., Imarisio S, Pineau S, Cordenier A, Maglathlin R L., Webster J A., Lewis [nl]T A., OKane C J., Schreiber S L., Rubinsztein D C., Nat. Chem. Biol. 2007 3 331
70. Peng Z.-H, Journet M, Humphrey G, Org. Lett. 2006 8 395
71. Isolation
72. Miller C O., Skoog F, Von Saltza M H., Strong F M., J. Am. Chem. Soc. 1955 77 1392
73. Miller C O., Skoog F, Okumura F S., Von Saltza M H., Strong F M., J. Am. Chem. Soc. 1956 78 1375
74. Villar J D. F., Motta M A., Nucleosides, Nucleotides Nucleic Acids 2000 19 1005
75. Barciszewski J, Mielcarek M, Stobiecki M, Siboska G, Clark B F. C., Biochem. Biophys. Res. Commun. 2000 279 69
76. For a recent review on kinetin, see:, Barciszewski J, Rattan S I. S., Siboska G, Clark B F. C., Plant Sci. 1999 148 37
77. For representative biological activities, see
78. Hartwell [nl]L H., Kastan M B., Science (Washington, DC, U.S.) 1994 266 1821
79. Nugiel D A., Cornelius L A. M., Corbett J W., J. Org. Chem. 1997 62 201
80. Dorff P H., Garigipati R S., Tetrahedron Lett. 2001 42 2771
81. Hammarstrm L G. J., Smith D B., Talams F X., Labadie S S., Krauss [nl]N E., Tetrahedron Lett. 2002 43 8071
82. Levins C G., Wan Z.-K, Org. Lett. 2008 10 1755; and references cited therein for conventional syntheses
83. Madhavan R, Srinivasan V R., Indian J. Chem. 1969 7 760
84. Confalone P N., Woodward R B., J. Am. Chem. Soc. 1983 105 902
85. Deshmukh M B., Shelar M A., Mulik A R., Indian J. Heterocycl. Chem. 2000 10 13
86. Laddi U V., Desai S R., Bennur R S., Bennur S C., Indian J. Heterocycl. Chem. 2002 11 319
87. Honnalli S S., Ronad P M., Vijaybhasker K, Jukkeri V I., Kumar R, Heterocycl. Commun. 2005 11 505
88. Smith A E. W., Science (Washington, DC, U.S.) 1954 119 514
89. Stempel A, Zelauskas J, Aeschlimann J A., J. Org. Chem. 1955 20 412
90. Rosen G M., Popp F D., Gemmill F Q. Jr., J. Heterocycl. Chem. 1971 8 659
91. Thompson S K., Smith W W., Zhao B, Halbert S M., Tomaszek T A., Tew D G., Levy M A., Janson C A., DAlessio K J., McQueney M S., Kurdyla J, Jones C S., DesJarlais R L., Abdel-Meguid S S., Veber D F., [nl]J. Med. Chem. 1998 41 3923
92. Grzyb J A., Dekeyser M A., Batey R A., Synthesis 2005 2384
93. Clemens J J., Davis M D., Lynch K R., Macdonald T L., Bioorg. Med. Chem. Lett. 2004 14 4903
94. Anand N K., Blazey C M., Bowles O J., Bussenius J, CanneBannen L, Chan D S.-M, Chen B, Co E W., Costanzo S, Defina S C., Dubenko L, Franzini M, Huang P, Jammalamadaka V, Khoury R G., Kim M H., Klein R R., Le D T., Mac M B., Nuss J M., Parks J J., Rice K D., Tsang T, Tsuhako A L., Wang Y, Xu W, WO 2005117909
95. Pritz S, Wolf Y, Klemm C, Bienert M, Tetrahedron Lett. 2006 47 5893
96. Kang F.-A, Kodah J, Guan Q, Li X, Murray W V., [nl] J. Org. Chem. 2005 70 1957
97. Kang F.-A, Sui Z, Murray W V., Eur. J. Org. Chem. 2009 461
98. Ashton T D., Scammells P J., Aust. J. Chem. 2008 61 49
99. For example, the amination of guanosine proceeded much better with DBU in acetonitrile: Wan, Z.-K.; Binnun, E. unpublished results., Lakshman M K., Frank J, Org. Biomol. Chem. 2009 7 2933
100. Ashton T D., Baker S P., Hutchinson S A., Scammells P J., Bioorg. Med. Chem. 2008 16 1861
101. Bae S, Lakshman M K., J. Am. Chem. Soc. 2007 129 782
102. Xiao Z, Yang M G., Li P, Carter P H., Org. Lett. 2009 11 1421
103. Boge N, Kruger S, Schroder M, Meier C, Synthesis 2007 3907
104. Rabisson P, Lenz O, Lin T.-I, Surleraux D, Chakravarty S, Scholliers A, Vermeiren K, Delouvroy F, Vervinnen T, Simmen K, Bioorg. Med. Chem. Lett. 2007 17 1843
105. Scicinski J J., Congreve M S., Jamieson C, Ley S V., Newman E S., Vinader V M., Carr R A. E., J. Comb. Chem. 2001 2 387
106. Hisamichi H, Naito R, Toyoshima A, Kawano N, Ichikawa A, Orita A, Orita M, Hamada N, Takeuchi M, Ohta M, Tsukamoto S.-i, Bioorg. Med. Chem. 2005 13 4936
107. Hisamichi H, Naito R, Toyoshima A, Kawano N, Ichikawa A, Orita A, Orita M, Hamada N, Takeuchi M, Ohta M, Tsukamoto S.-i, Bioorg. Med. Chem. 2005 13 6277
108. Reese C B., Richards K H., Tetrahedron Lett. 1985 26 2245
109. Nagashima S, Yokota M, Nakai E.-i, Kuromitsu S, Ohga K, Takeuchi M, Tsukamoto S.-i, Ohta M, Bioorg. Med. Chem. 2007 15 1044
110. For a recent review on benzotriazole chemistry, see:, Katritzky A R., Rachwal S, Chem. Rev. 2009 DOI: 10.1021/cr900204u
111. Bae S, Lakshman M K., J. Org. Chem. 2008 73 3707
112. Bae S, Lakshman M K., Org. Lett. 2008 10 2203
113. Kang F.-A, Sui Z, Murray W V., J. Am. Chem. Soc. 2008 130 11300
114. Wacharasindhu S, Bardhan S, Wan Z.-K, Tabei K, Mansour T S., J. Am. Chem. Soc. 2009 131 4174
115. Long T, Burgess K, Chemtracts 1998 11 1037; and references cited therein
116. Bardhan S, Wacharasindhu S, Wan Z.-K, Mansour T S., Org. Lett. 2009 11 2511
117. Navarro O, Kaur H, Mahjoor P, Nolan S P., J. Org. Chem. 2004 69 3173
118. Li S, Lin Y, Cao J, Zhang S, J. Org. Chem. 2007 72 4067
119. Kirchhoff J H., Netherton M R., Hills I D., Fu G C., J. Am. Chem. Soc. 2002 124 13662
120. Miyaura N, Suzuki A, Chem. Rev. 1995 95 2457
121. Suzuki A, Pure Appl. Chem. 1991 63 419
122. For Buchwalds phosphine ligand (DTBBP), see:, Aranyos A, Old D W., Kiyomori A, Wolfe J P., Sadighi J P., Buchwald S L., J. Am. Chem. Soc. 1999 121 4369
123. Adamo C, Amatore C, Ciofini I, Jutand A, Lakmini H, J. Am. Chem. Soc. 2006 128 6829
124. Aramendia [nl]M A., Lafont M, Moreno-Manas M, Perez M, Pleixats R, J. Org. Chem. 1999 64 3592
125. Hossain K M., Kameyama T, Shibata T, Tagaki K, Bull. Chem. Soc. Jpn. 2001 74 2415
126. Wong M S., Zhang X L., Tetrahedron Lett. 2001 42 4087
127. Yoshida H, Yamaryo Y, Ohshita J, Kunai A, Tetrahedron Lett. 2003 44 1541
128. Hatamoto Y, Sakaguchi S, Ishii Y, Org. Lett. 2004 6 4623
129. Yamamoto Y, Suzuki R, Hattori K, Nishiyama H, Synlett 2006 1027
130. Stahl S S., Angew. Chem. Int. Ed. 2004 43 3400
131. Popp B V., Stahl S S., [nl] J. Am. Chem. Soc. 2006 128 2804
132. Yoo K S., Yoon C H., Jung K W., J. Am. Chem. Soc. 2006 128 16384
133. Bardhan S, Tabei K, Wan Z.-K, Mansour T S., Tetrahedron Lett. 2009 50 5733
134. Katritzky A R., Kurz T, Zhang S, Voronkov M, Heterocycles 2001 55 1703
135. Carpino L A., Imazumi H, El-Faham A, Ferrer F J., Zhang C, Lee Y, Foxman M M., Henklein P, Hanay C, Mugge C, Wenschuh H, Klose J, Beyermann M, Bienert M, Angew. Chem. Int. Ed. 2002 41 442