Recent applications of 2,4,6-trichloro-1,3,5-triazine and its derivatives in organic synthesis

Tetrahedron

Volumn 62, Issue 41, 2006, Pages 9507-9522

  Blotny, Grzegorz ^a  

^a UNIVERSITY OF MARYLAND BALTIMORE COUNTY   (United States)

Author keywords

2,4,6 Trichloro 1,3,5 triazine; 2 Chloro 4,6 dimethoxy s triazine; Functional group transformations

Indexed keywords

2 CHLORO 4,6 DIMETHOXY 1,3,5 TRIAZINE; 2,4,6 TRICHLORO 1,3,5 TRIAZINE; 4 (4,6 DIMETHOXY 1,3,5 TRIAZIN 2 YL) 4 METHYLMORPHOLINIUM; 4 METHYLMORPHOLINE; ALPHA AMINO ACID; CHLORIDE; CYANURIC ACID; CYANURIC CHLORIDE; DENDRIMER; MORPHOLINE DERIVATIVE; SYMCLOSENE; TRIAZINE; TRIAZINE DERIVATIVE; UNCLASSIFIED DRUG;

CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHLORINATION; MICROWAVE RADIATION; NEUTRON CAPTURE THERAPY; OXIDATION; PRIORITY JOURNAL; REVIEW; ROOM TEMPERATURE; SOLID; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS; TEMPERATURE DEPENDENCE;

EID: 33748684468     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.07.039     Document Type: Review

References (120)

1. Smolin E.M., and Rapoport L. s-Triazine and Derivatives in The Chemistry of Heterocyclic Compounds (1959), Interscience, New York, NY
2. Mur V.I. Russ. Chem. Rev. 33 (1964) 92-103 and references therein
3. Quirke M.E. 1,3,5-Triazines. In: Katritzky A.R., and Rees C.W. (Eds). Comprehensive Heterocyclic Chemistry Vol. 3 (1984), Pergamon, New York, NY 457-530
4. Bartholomew D. 1,3,5-Triazines. In: Boulton A.J. (Ed). Comprehensive Heterocyclic Chemistry II Vol. 6 (1996), Pergamon, Oxford 575
5. Comins D.L., and Ó'Connor. In: Katritzky A.R. (Ed). Advances in Heterocyclic Chemistry Vol. 44 (1988), Academic, New York, NY 243
6. Giacomelli G., Porcheddu A., and De Luca L. Curr. Org. Chem. 8 (2004) 1497-1519
7. Menicagli R., Malanga C., and Peluso P. Synth. Commun. 24 (1994) 2153-2158
8. Samaritani S., Peluso P., Malanga C., and Menicagli R. Eur. J. Org. Chem. (2002) 1551-1555
9. Moon H.-S., Jacobson E.M., Khersonsky S.M., Luzung M.R., Walsh D.P., Xiong W., Lee J.W., Parikh P.B., Lam J.C., Kang T.-W., Rosania G.R., Schier A.F., and Chang Y.-T. J. Am. Chem. Soc. 124 (2002) 11608-11609
10. Bork J.T., Lee J.W., and Cheng Y.-T. Tetrahedron Lett. 44 (2003) 6141-6144
11. Bork J.T., Lee J.W., Khersonsky S.M., Moon H.-M., and Chang Y.-T. Org. Lett. 5 (2003) 117-120
12. Hollink E., Simanek E.E., and Bergbreiter D.E. Tetrahedron Lett. 46 (2005) 2005-2008
13. Falorni M., Giacomelli G., Mameli L., and Porcheddu A. Tetrahedron Lett. 39 (1998) 7607-7610
14. Tahmassebi D.C., and Sasaki T. J. Org. Chem. 59 (1994) 679-681
15. Tahmassebi D.C., and Sasaki T. J. Org. Chem. (1998) 728-731
16. Shin Y., Liu J., Wang L.-Q., Nie Z., Samuels W.D., Fryxell G.E., and Exarhos G.J. Angew. Chem., Int. Ed. 39 (2000) 2702-2707
17. Gustafson G.R., Baldino C.M., O'Donnell M.-M., Sheldon A., Tarsa R.J., Verni C.J., and Coffen D.L. Tetrahedron 54 (1998) 4051-4065
18. Varaprasad C.V., Habib Q., Li D.Y., Huang J., Abt J.W., Rong F., Hong Z., and An H. Tetrahedron 59 (2003) 2297-2307
19. Hysell M., Siegel J.S., and Tor Y. Org. Biomol. Chem. 3 (2005) 2946-2952
20. Yang X., and Lowe C.R. Tetrahedron Lett. 44 (2003) 1359-1362
21. Wang M.-X., and Yang H.-B. J. Am. Chem. Soc. 126 (2004) 15412-15422
22. Löwik D.W.P.M., and Lowe C.R. Eur. J. Org. Chem. (2001) 2825-2839
23. Engrand P., and Regnouf-de-Vains J.-B. Tetrahedron Lett. 43 (2002) 8863-8866
24. Carofiglio T., Varotto A., and Tonellato U. J. Org. Chem. 69 (2004) 8121-8124
25. Ichihara K., and Naruta Y. Chem. Lett. (1995) 631-632
26. Zerkowski J.A., Hensley L.M., and Abramowitz D. Synlett (2002) 557-560
27. Azev Y.A., Dülcks T., and Gabel D. Tetrahedron Lett. 44 (2003) 8689-8691
28. Lee C.-H., Lim H.-G., Nakamura H., and Kang S.O. Appl. Organomet. Chem. 17 (2003) 539-548
29. Ronchi S., Prosperi D., Compostella F., and Panza L. Synlett (2004) 1007-1010
30. McNamara C.A., King F., and Bradley M. Tetrahedron Lett. 45 (2004) 8527-8529
31. Guo Q., Xie Y., Wang X., Zhang S., Hou T., and Lv S. Chem. Commun. (2004) 26-27
32. Pozzi G., Cavazzini M., Holczknecht O., Quici S., and Shepperson I. Tetrahedron Lett. 45 (2004) 4249-4251
33. Piera E., Comelles F., Erra P., and Infante M.R. J. Chem. Soc., Perkin Trans. 2 (1998) 335-342
34. Zhang W., and Simanek E.E. Org. Lett. 2 (2000) 843-845
35. Zhang W., Nowlan D.T., Thomson L.M., Lackowski W., and Simanek E.E. J. Am. Chem. Soc. 123 (2001) 8914-8922
36. Zhang W., and Simanek E.E. Tetrahedron Lett. 42 (2001) 5355-5357
37. Zhang W., Tichy S.E., Pérez L.M., Maria G.C., Lindahl P.A., and Simanek E.E. J. Am. Chem. Soc. 125 (2003) 5086-5094
38. Steffensen M., and Simanek E.E. Angew. Chem., Int. Ed. 43 (2004) 5178-5180
39. Chen H.-T., Neerman M.F., Parrish A.R., and Simanek E.E. J. Am. Chem. Soc. 126 (2004) 10044-10048
40. Steffensen M.B., and Simanek E.E. Org. Lett. 5 (2003) 2359-2361
41. Lai L.L., Wang L.Y., Lee C.H., Lin Y.C., and Cheng K.L. Org. Lett. 8 (2006) 1541-1544
42. Lehn J.M., Mascal M., DeCian A., and Fisher J. J. Chem. Soc., Chem. Commun. (1990) 479-480
43. Mathias J.P., Seto C.T., Simanek E.E., and Whitesides G.M. J. Am. Chem. Soc. 116 (1994) 1725-1736
44. Timmerman P., Weidemann J.-L., Jolliffe K.A., Prins L.J., Reinhoudt D.N., Shinkai S., Frish L., and Cohen Y. J. Chem. Soc., Perkin Trans. 2 (2000) 2077-2089
45. Lipkowski P., Bielejewska A., Kooijman H., Spek A.L., Timmerman P., and Reinhoudt D.N. Chem. Commun. (1999) 1311-1312
46. Prins L.J., Jolliffe K.A., Hulst R., Timmerman P., and Reinhoudt D.N. J. Am. Chem. Soc. 122 (2000) 3617-3627
47. Prins L.J., Neuteboom E.E., Parashiv V., Crego-Calama M., Timmerman P., and Reinhoudt D.N. J. Org. Chem. 67 (2002) 4808-4820
48. Arduini M., Crego-Calama M., Timmerman P., and Reinhoudt D.N. J. Org. Chem. 68 (2003) 1097-1106
49. Archer E.A., Goldberg N.T., Lynch V., and Krische M.J. J. Am. Chem. Soc. 122 (2000) 5006-5007
50. Archer E.A., Cauble D.F., Lynch V., and Krische M.J. Tetrahedron 58 (2002) 721-725
51. Archer E.A., and Krische M.J. J. Am. Chem. Soc. 124 (2002) 5074-5083
52. Timmerman P., Vreekamp R.H., Hulst R., Verboom W., Reinhoudt D.N., Rissanen K., Udachin K.A., and Ripmeester J. Chem.-Eur. J. 3 (1997) 1823-1832
53. Perdigao L.M.A., Champness N.R., and Beton H.P. Chem. Commun. (2006) 538-540
54. Lawrence D.S., Jiang T., and Levett M. Chem. Rev. 95 (1995) 2229-2260
55. Conn M.M., and Rebek Jr. J. Chem. Rev. 97 (1997) 1647-1668
56. Timmerman P., and Prins L.J. Eur. J. Org. Chem. (2001) 3191-3205
57. Mateos-Timoneda M.A., Crego-Calama M., and Reinhoudt D.N. Chem.-Eur. J. 12 (2006) 2630-2638
58. Larock R.C. Comprehensive Organic Transformation (1989), VCH, New York, NY
59. Senier A. Chem. Ber. 19 (1886) 310-312
60. Sandler S.R. J. Org. Chem. 35 (1970) 3967-3970
61. Venkataramen K., and Wagle D.R. Tetrahedron Lett. 32 (1979) 3037-3040
62. Lahoti R.J., and Wagle D.R. Indian J. Chem. 20B (1981) 852-855
63. Lahoti R.J., and Wagle D.R. Indian J. Chem. 20B (1981) 1007-1008
64. Olah G.A., Fung A.P., Gupta B.G.B., and Narang S.C. Synthesis (1980) 221
65. Olah G.A., Narang S.C., Fung A.P., and Gupta B.G.B. Synthesis (1980) 657-658
66. Chakrabarti J.K., and Hotten T.M. J. Chem. Soc., Chem. Commun. (1972) 1226-1227
67. Luo G., Xu L., and Poindexter G.S. Tetrahedron Lett. 43 (2002) 8909-8912
68. Falorni M., Porcheddu A., and Tadei M. Tetrahedron Lett. 40 (1999) 4395-4396
69. Masala S., and Tadei M. Org. Lett. 1 (1999) 1355-1357
70. Rayle H.L., and Fellmeth L. Org. Process Res. Dev. 3 (1999) 172-176
71. Forbes D.C., Barrett E.J., Lewis D.L., and Smith M.C. Tetrahedron Lett. 41 (2000) 9943-9947
72. Bandgar B.P., and Pandit S.S. Tetrahedron Lett. 43 (2002) 3413-3414
73. Kaminski Z.J. Biopolimers (Pept. Sci) 55 (2000) 140-164
74. Giacomelli G., Porcheddu A., and Salaris M. Org. Lett. 5 (2003) 2715-2717
75. Blotny G. Tetrahedron Lett. 44 (2003) 1499-1501
76. De Luca L., Giacomelli G., and Porcheddu A. Organic Lett. 4 (2002) 553-555
77. Gold H. Angew. Chem. 72 (1960) 956-959
78. De Luca L., Giacomelli G., and Porcheddu A. J. Org. Chem. 67 (2002) 5152-5155
79. De Luca L., Giacomelli G., and Porcheddu A. J. Org. Chem. 67 (2002) 6272-6274
80. Furuya Y., Ishihara K., and Yamamoto H. J. Am. Chem. Soc. 127 (2005) 11240-11241
81. Karimi B., Hazarkhami H., and Zareyee D. Synthesis (2002) 2513-2516
82. De Luca L., Giacomelli G., and Porcheddu A. J. Org. Chem. 66 (2001) 7907-7909
83. Karimi B., and Hazarkhani H. Synthesis (2003) 2547-2551
84. Porcheddu A., Giacomelli G., and Salaris M. J. Org. Chem. 70 (2005) 2361-2363
85. Merifield R.B. J. Am. Chem. Soc. 85 (1963) 2149-2154
86. Kates S.A., and Albericio F. Solid-Phase Synthesis: A Practical Guide (2000), Marcel Dekker, New York, NY
87. Falchi A., and Tadei M. Org. Lett. 2 (2000) 3429-3431
88. Marsh A., Carlisle S.J., and Smith S.C. Tetrahedron Lett. 42 (2001) 493-496
89. Cronin J.S., Ginah F.O., Murray A.R., and Copp J.D. Synth. Commun. 26 (1996) 3491-3494
90. Kaminski Z.J., Paneth P., and Rudzinski J. J. Org. Chem. 63 (1998) 4248-4255
91. Kaminski Z.J., Kolesinska B., Kaminska J.E., and Gora J. J. Org. Chem. 66 (2001) 6276-6281
92. Garrett C.E., Jiang X., Prasad K., and Repic O. Tetrahedron Lett. 43 (2002) 4161-4165
93. Kunishima M., Kawachi C., Iwasaki F., Terao K., and Tani S. Tetrahedron Lett. 40 (1999) 5327-5330
94. Kunishima M., Kawachi C., Morita J., Terao K., Iwasaki F., and Tani S. Tetrahedron 55 (1999) 13159-13170
95. Kunishima M., Morita J., Kawachi C., Iwasaki F., Terao K., and Tani S. Synlett (1999) 1255-1256
96. Kunishima M., Kawachi C., Hioki K., Terao K., and Tani S. Tetrahedron 57 (2001) 1551-1558
97. Falchi A., Giacomelli G., Porcheddu A., and Taddei M. Synlett (2000) 275-277
98. Kaminski Z.J., Kolesinska B., Kolesinska J., Sabatino G., Chelli M., Rovero P., Blaszczyk M., Glowka M.L., and Papini A.M. J. Am. Chem. Soc. 127 (2005) 16912-16920
99. De Luca L., Giacomelli G., and Taddei M. J. Org. Chem. 66 (2001) 2534-2537
100. Nahm S., and Weinreb S.M. Tetrahedron Lett. 22 (1981) 3815-3818
101. Falorni M., Giacomelli G., Porcheddu A., and Tadei M. J. Org. Chem. 64 (1999) 8962-8964
102. De Luca L., Giacomelli G., and Porcheddu A. Org. Lett. 3 (2001) 1519-1521
103. Bandgar B.P., and Pandit S.S. Tetrahedron Lett. 44 (2003) 2331-2333
104. Bandgar B.P., and Pandit S.S. Tetrahedron Lett. 44 (2003) 3855-3858
105. De Luca L., Giacomelli G., Porcheddu A., and Salaris M. Synlett (2004) 2570-2572
106. Kunishima M., Yamamoto K., Watanabe Y., Hioki K., and Tani S. Chem. Commun. (2005) 2698-2700
107. Markowicz M.W., and Dembinski R. Synthesis (2004) 80-86
108. Olah G.A., Nojima M., and Kerekes I. Synthesis (1973) 487-488
109. Karygiannis G., Athanassopoulos C., Mamos P., Karamanos N., Papaioannou D., and Francis G.W. Acta Chem. Scand. 52 (1998) 1144-1150
110. Carpino, L. A.; Ionescu, D.; El-Faham, A.; Beyermann, M.; Henklein, P.; Hanay, C.; Wenschuh, H.; Bienert, M. Org. Lett. 2003, 5, 975-977 and references therein.
111. Tilstam U., and Weinmann H. Org. Process Res. Dev. 6 (2002) 384-393
112. De Luca L., Giacomelli G., and Porcheddu A. Org. Lett. 3 (2001) 3041-3043
113. Zolfigol M.A., Shirini F., and Choghamarani A.G. Synthesis (2006) 2043-2046
114. Chen F.-E., Kuang Y.-Y., Dai, Lu L., and Huo M. Synthesis (2003) 2629-2631
115. Frouzabadi H., Iranpoor N., and Hazarkhani H. Synlett (2001) 1641-1643
116. Zolfigol M.A., Azarifar D., and Maleki B. Tetrahedron Lett. 45 (2004) 2181-2183
117. De Luca L., Giacomelli G., and Nieddu G. Synlett (2005) 223-226
118. Rodrigues R.C., Barros I.M.A., and Lima E.L.S. Tetrahedron Lett. 46 (2005) 5945-5947
119. Acharya J., Gupta A.K., Shakya P.D., and Kaushik M.P. Tetrahedron Lett. 46 (2005) 5293-5295
120. Hioki K., Kinugasa M., Kishimoto M., Fujiwara M., Tani S., and Kunishima M. Synthesis (2006) 1931-1933