An insight into hexamethylenetetramine: A versatile reagent in organic synthesis

Journal of the Iranian Chemical Society

Volumn 10, Issue 6, 2013, Pages 1193-1228

  Kaur, Navjeet ^a   Kishore, Dharma ^a  

^a BANASTHALI UNIVERSITY   (India)

Author keywords

Hexamethylenetetramine; Organic synthesis; Reagent

Indexed keywords

EID: 84886938972     PISSN: 1735207X     EISSN: 17352428     Source Type: Journal    
DOI: 10.1007/s13738-013-0260-2     Document Type: Article

References (116)

1. M. Fatehi, J. Ethnopharmacol. 102, 46 (2005)
2. J.C. Duff, E.J. Bills, J. Chem. Soc. 547, 276 (1945)
3. P.L. Henaff, C.R. Acad, Sci. Paris 253, 2706 (1961)
4. I.M. Lapina, A.A. Pevzner, A.A. Potekhin, Russ. J. Gen. Chem. 76, 1304 (2006)
5. N. Blazevic, D. Kolbah, Synthesis, 3, 161 (1979)
6. D.J. Daigle, A.B. Pepperman, S.L. Vail, J. Heterocycl. Chem. 11, 407 (1974)
7. D.J. Daigle, A.B. Pepperman, US Patent 391, 189 (1973); C.A. 81 (1974) 120 788
8. D.J. Daigle, A.B. Pepperman, J. Heterocycl. Chem. 12, 579 (1975)
9. D.J. Daigle, A.B. Pepperman, G. Bondreaux, J. Heterocycl. Chem. 11, 1085 (1974)
10. H.E. Baumgarten, F.A. Bower, J. Am. Chem. Soc. 76, 4651 (1954)
11. S.W. Kshirsagar, N.R. Patil, S.D. Samant, Tetrahedron Lett. 49, 1160 (2008)
12. A.T. Bottini, V. Dev, J. Org. Chem. 27, 968 (1962)
13. H.J. Naeimi, Chin. Chem. Soc. 55, 1156 (2008)
14. E.V. Zakharov, S.A. Balezin, E.S. Murashova, N.J. Ivanov, N.V. Lardash, Zh. Prikl. Khim. 47, 2351 (1974)
15. G. Olkoks, Geterocikliceskie Soedineija I Polimeri na jih osnove, Mir, Moskva, 22, 136 (1970)
16. O.P. Murashova, L.I. Virin, V.R. Rozenberg, G.V. Motsarev, V.J. Kolbasov, Y.A. Safin, R.V. Dzhagatspanyan, Zh. Prikl. Khim. 48, 1802 (1975)
17. G.L. Nemchanimova, K.E. Peredelskiy, Zh. Prikl. Khim. 47, 1879 (1974)
18. X.H. Xu, B. Chen, L.Z. Wu, L.P. Zhang, C.H. Tung, ARKIVOC ii, 182 (2003)
19. E. Reimann, Justus Liebigs Ann. Chem. 1252, 7 (1975)
20. S. Cheronis, J. Org. Chem. 6, 349 (1945)
21. A. Adejare, S. Sun, Curr. Top. Med. Chem. 6, 1457 (2006)
22. S.A. Chimatadar, S.V. Madawale, S.T. Nandibewoor, Ind. J. Chem. Technol. 14, 459 (2007)
23. J.C. Hoekstra, D.C. Johnson, Anal. Chem. 70, 83 (1998)
24. J. March, Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 3rd edn. (Wiley, New York, 1985). ISBN 0-471-85472-7
25. M. Thompson, J. Whelan, D.J. Zemon, B. Bosnich, E.I. Solomon, H.B. Gray, J. Am. Chem. Soc. 101, 2483 (1979)
26. J.S. McFadyen, T.S. Stevens, J. Chem. Soc. 6, 584 (1936)
27. A.R. Katritzky, Y. He, Q. Long, A.L. Wilcox, ARKIVOC iii, 3 (2001)
28. A. Nicolae, C. Drghici, A. David, Rev. Chim. 34, 789 (2003)
29. G. Serban, S. Cuc, E. Egri, A. Salvan, Farmacia 58, 6 (2010)
30. H.C. Brown, B.C. Rao, J. Am. Chem. Soc. 80, 5377 (1958)
31. T. Brown, J. Am. Chem. Soc. 81, 502 (1959)
32. H. Fieser, J. Am. Chem. Soc. 62, 52 (1940)
33. J.C. Duff, V.J. Furness, J. Chem. Soc. 9, 1512 (1951)
34. A.V. Zaytsev, R.J. Anderson, A. Bedernjak, P.W. Groundwater, Y. Huang, J.D. Perry, S. Orenga, C. Dalbert, A. James, Org. Biomol. Chem. 6, 682 (2008)
35. S.R. Chaudhuri, A. Modak, A. Bhaumik, S. Swarnakar, Int. J. Pharma. App. 4, 237 (2011)
36. M. Pepper, Can. J. Chem. 31, 476 (1953)
37. L. Campaigne, J. Am. Chem. Soc. 70, 1555 (1948)
38. J. Hartough, Am. Chem. Soc. 69, 1355 (1947)
39. N. Masurier, E. Moreau, C. Lartigue, V. Gaumet, J. Chezal, A. Heitz, J. Teulade, O. Chavignon, J. Org. Chem. 73, 5989 (2008)
40. S.J. Angyal, R.C. Rassack, Nature 161, 723 (1948)
41. C.S. Marvel, Org. Syn. 2, 310 (1943)
42. C.S. Marvel, Org. Syn. 14, 46 (1934)
43. A.R.N. Shenoy, P.R. Shankaran, S.B. Rao, Ind. J. Pharm. 34, 48 (1972)
44. M. Mihalic, F. Sunjic, P. Mildner, F. Kajfez, Croat. Chem. Acta 48, 125 (1976)
45. K. Ishizumi, K. Mori, Y. Komeno, J. Katsube, H. Yamamoto, Japanese Patent, (1977) 7739690, C.A. 87, 152 287
46. K. Ishizumi, Y. Komeno, K. Mori, J. Katsube, Japanese Patent, (1977) 7739690, C.A. 87, 152 287
47. M. Ogata, H. Mastsumoto, Chem. Ind. (London), 7, 1067 (1976)
48. P. Sharma, B. Vashistha, R. Tyagi, V. Srivastava, M. Shorey, B. Singh, D. Kishore, Int. J. Chem. Sci. 8, 41 (2010)
49. M. Baumann, I.R. Baxendale, S.V. Ley, N. Nikbin, Beilstein J. Org. Chem. 7, 442 (2011)
50. C. Pi, Z. Quan, M. Yun-Bao, J. Zhi-Yong, Z. Xue-Mei, Z. Feng-Xue, C. Ji-Jun, Bioorg. Med. Chem. Lett. 18, 3787 (2008)
51. B. Ahmad, M. Rashid, A. Husain, R. Mishra, Ind. J. Chem. 51B, 639 (2012)
52. A. Javidan, M.B. Yzaamnian, H. Zabarjadan, N. Anikeev, A.I. Petrunin, M.T. Kilin, F.V. Guss, Pharm. Chem. J. 38, 261 (2004)
53. L.H. Sternbach, R.I. Fryer, W. Metlesics, E. Reeder, G. Sach, G. Saucy, A. Stemple, J. Org. Chem. 27, 3788 (1962)
54. D. Lednicer, The Organic Chemistry of Drug Synthesis (Wiley-Interscience, New York, 1998)
55. M. Rashid, B. Ahmad, R. Mishra, Int. J. Ph. Sci. 2, 616 (2012)
56. P.V.G. Reddy, Y.W. Lin, H.T. Chang, ARKIVOC xvi, 113 (2007)
57. B. Cekavicus, B. Vigante, E. Liepinsh, R. Vilskersts, A. Sobolev, S. Belyakov, A. Plotniece, K. Mekss, G. Duburs, Tetrahedron 64, 9947 (2008)
58. T.B. Reddy, Y.V.R. Reddy, J. Chem. Pharm. Res. 3, 617 (2011)
59. S.O. Simonetti, E.L. Larghi, A.B.J. Bracca, T.S. Kaufman, Org. Biomol. Chem. 10, 4124 (2012)
60. K.S.S. Lamani, O. Kotresh, M.A. Phaniband, J.C. Kadakol, E-J. Chem. 6, 239 (2009)
61. R.M. Zaki, S.M. Radwan, A.M.K. El-Dean, J. Chin. Chem. Soc. 58, 544 (2011)
62. K.C. Majumdar, U. Das, U.K. Kundu, A. Bandyopadhyay, Tetrahedron 57, 7003 (2001)
63. G. Kaupp, K.J. Sailer, Prakt. Chem. 338, 47 (1996)
64. E. Kessler, Monatsh. Chem. 98, 1512 (1967)
65. N. Blazevic, V. Sunjic, I. Crvelin, D. Kolbah, F. Kajfez, J. Heterocycl. Chem. 9, 531 (1972)
66. C. Dauth, H.G.O. Becker, J. Prakt. Chem. 312, 440 (1970)
67. H. Mohrle, B. Gusowski, Chem. Ber. 106, 2485 (1973)
68. N. Kuwabara, H. Hayashi, N. Hiramatsu, T. Choshi, E. Sugino, S. Hibino, Chem. Pharm. Bull. 47, 1805 (1999)
69. G. Serban, S. Cuc, E. Egri, A. Salvan, Farmacia 58, 818 (2010)
70. D. Kumar, S. Sundaree, G. Patel, V.S. Rao, Tetrahedron Lett. 49, 867 (2008)
71. S. Mahboobi, E.C. Fischer, E. Eibler, W. Wiegrebe, Arch. Pharm. 321, 423 (1988)
72. A.I. Meyers, J.S. Warmus, G.J. Dilley, Org. Syn. 9, 666 (1998)
73. A.I. Meyers, J.S. Warmus, G.J. Dilley, Org. Syn. 73, 246 (1996)
74. N. Blazevic, M. Oklobdzija, V. Sunjic, F. Kajfez, D. Kolbah, Acta Pharm. Jugosl. 25, 223 (1975)
75. S.L. Schreiber, J. Liu, M.W. Albers, R. Karmacharya, E. Koh et al., Transpl. Proc. 23, 2839 (1991)
76. D.I. Pritchard et al., United States Patent 7482362. 27, 01 (2009)
77. W. Brown, C. Foote, Organic Chemistry, 3rd edn. (Harcourt College, Philadelphia, 2002)
78. R.I. Fryer, L.H. Sternbach, J. Org. Chem. 30, 524 (1965)
79. K.K.C. Liu, S.M. Sakya, C.J. O'Donnell, A.C. Flick, J. Li, Bioorg. Med. Chem. 19, 1136 (2011)
80. W.E. Bachmann, N.C. Deno, J. Am. Chem. Soc. 73, 2777 (1951)
81. V.I. Siele, M. Warman, E.E. Gilbert, J. Heterocycl. Chem. 11, 237 (1974)
82. Y. Ogata, A. Kawasaki, in The Chemistry of the Carbonyl Group, 2nd edn., ed. by J. Zabicky (Wiley Interscience, New York, 1970), p. 51
83. H. Yoshida, G. Sen, B.S. Thyagarajan, J. Heterocycl. Chem. 10, 279 (1973)
84. R. Emmons, R. Cannon, J. Am. Chem. Soc. 74, 5524 (1952)
85. P. Rajakumara, R. Padmanabhan, ARKIVOC, vi (2012) 155
86. P. Galimberti, C. Erba, Gazz. Chim. Ital. 77, 375 (1947)
87. W.J. Burke, M.J. Kolbezen, R.J. Reynolds, G.A. Short, J. Am. Chem. Soc. 78, 805 (1956)
88. U. Takaki, J. Pharm. Soc. Jpn 58, 276 (1938)
89. S.W. Kantor, C.R. Hauser, J. Am. Chem. Soc. 73, 4122 (1951)
90. S. Liangwei, Y. Menglong, Z. Yazhu, Q. Guangming, L. Jian, Z. Gang, Chin. J. Chem. 29, 283 (2011)
91. W.J. Chute, D.C. Downing, A.F. McKay, G.S. Myers, G.F. Wright, Can. J. Res. 27B, 218 (1949)
92. W.J. Chute, A.F. McKay, R.H. Meen, G.S. Myers, G.F. Wright, Can. J. Res. 27B, 503 (1949)
93. E.N. Jacobsen, L. Deng, Y. Furukawa, L.E. Martinez, Tetrahedron 50, 4323 (1994)
94. A.B. Antonova, Coord. Chem. Rev. 251, 1521 (2007)
95. M.W. Tinsay, K. Siraj, Eur. J. Sci. Res. 49, 49 (2011)
96. H.E. Baumgarten, J.M. Petersen, Org. Syn. 5, 909 (1973)
97. H.E. Baumgarten, J.M. Petersen, Org. Syn. 41, 82 (1961)
98. F. Couturier, Ann. Chim. 10, 610 (1938)
99. E.J. Schwoegler, H. Adkins, J. Am. Chem. Soc. 61, 3499 (1939)
100. J. Sekiya, Pharm. Soc. Jpn 70, 520 (1950)
101. B.P. Bandgar, S.B. Admaneb, S.S. Jareb, J. Chem. Res. (S), 2, 154 (1998)
102. M.M. Heravi, A.J. Sabaghiani, M. Bakavoli, M. Ghassemzadehc, K.J. Bakhtiari, Chin. Chem. Soc. 54, 123 (2007)
103. V. Bereau, V. Jubera, P. Arnaud, A. Kaiba, P. Guionneau, J. Sutter, Dalton Trans. 39, 2070 (2010)
104. C.C. Zeng, J.Y. Becker, J. Org. Chem. 69, 1053 (2004)
105. B. Liang, M. Dai, J. Chen, Z.J. Yang, Org. Chem. 70, 391 (2005)
106. M. Bakherad, A. Keivanloo, B. Bahramian, M. Hashemi, Tetrahedron Lett. 50, 1557 (2009)
107. T. Teratani, A. Ohtaka, T. Kawashima, O. Shimomura, R. Nomura, Synlett, 15, 2271 (2010)
108. A.K. Nezhad, F. Panahi, Green Chem. 13, 2408 (2011)
109. S. Hesse, Angew. Chem. 68, 438 (1956)
110. S. Hesse, Ann. 607, 24 (1957)
111. E. Fluck, P. Meiser, Angew. Chem. 83, 721 (1971)
112. E. Fluck, P. Meiser, Angew. Chem. Int. Ed. Engl. 10, 653 (1971)
113. E. Fluck, P. Meiser, Chem. Ber. 106, 69 (1973)
114. S.S. Kumar, F.M.I. Mohamed, Int. J. Pharm. Life Sci. 2, 1280 (2011)
115. S.S. Kumar, F.M.I. Mohamed, Int. J. Res. Chem. Environ. 2, 28 (2012)
116. A.N. Sarbaev, V.I. Kucheryavyi, L.M. Kozenko, Zh. Prikl. Khim. 42, 2528 (1969)