An easy access to functionalized allyl dithiocarbamates from Baylis-Hillman adducts in water

Tetrahedron Letters

Volumn 50, Issue 12, 2009, Pages 1335-1339

  Yadav, Lal Dhar S ^a   Patel, Rajesh ^a   Srivastava, Vishnu P ^a  

^a UNIVERSITY OF ALLAHABAD   (India)

Author keywords

1,3 Thiazines; Baylis Hillman adducts; Dithiocarbamates; Green procedure; Nucleophilic displacement; Stereoselective synthesis

Indexed keywords

ACETIC ACID; AMINE; ANION; CARBON DISULFIDE; DITHIOCARBAMIC ACID DERIVATIVE; NUCLEOPHILE; WATER;

ARTICLE; BAYLIS HILLMAN REACTION; SYNTHESIS;

EID: 59049099819     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.01.023     Document Type: Article

References (99)

1. Kondo T., and Mitsudo T.-A. Chem. Rev. 100 (2000) 3205-3220
2. Norcross R.D., and Paterson I. Chem. Rev. 95 (1995) 2041-2114
3. Faulkner D.J. Nat. Prod. Rep. 12 (1995) 223-269
4. Liu G., Link J.T., Pei Z., Reilly E.B., Leitza S., Nguyen B., Marsh K.C., Okasinski G.F., von Geldern T.W., Ormes M., Fowler K., and Gallatin M. J. Med. Chem. 43 (2000) 4025-4040
5. Sawyer J.S., Schmittling E.A., Palkowitz J.A., and Smith III W.J. J. Org. Chem. 63 (1998) 6338-6343
6. Trost B.M. Chem. Rev. 78 (1978) 363-382
7. Kita Y., Iio K., Kawaguchi K.-I., Fukuda N., Takeda Y., Ueno H., Okunaka R., Higuchi K., Tsujino T., Fujioka H., and Akai S. Chem. Eur. J. 6 (2000) 3897-3905
8. Dhooghe M., and De Kimpe N. Tetrahedron 62 (2006) 513-535
9. Erian A.W., and Sherif S.M. Tetrahedron 55 (1999) 7957-8024
10. Mukerjee A.K., and Ashare R. Chem. Rev. 91 (1991) 1-24
11. Boas U., Gretz H., Christensen J.B., and Heegaard P.M.H. Tetrahedron Lett. 45 (2004) 269-272
12. Grainger R.S., and Innocenti P. Heteroat. Chem. 18 (2007) 568-571
13. Rudorf W.-D. J. Sulfur Chem. 28 (2007) 295-339
14. Katritzky A.R., Singh S., Mohapatra P.P., Clemens N., and Kirichenko K. ARKIVOK ix (2005) 63-79
15. Caldas E.D., Conceicào M.H., Miranda M.C.C., de Souza L.C.K.R., and Lima J.F. J. Agric. Food Chem. 49 (2001) 4521-4525
16. Bowden K., and Chana R.S. J. Chem. Soc., Perkin Trans. 2 (1990) 2163-2166
17. Ronconi L., Marzano C., Zanello P., Corsini M., Miolo G., Macca C., Trevisan A., and Fregona D. J. Med. Chem. 49 (2006) 1648-1657
18. Elgemeie G.H., and Sayed S.H. Synthesis (2001) 1747-1771
19. Goel A., Mazur S.J., Fattah R.J., Hartman T.L., Turpin J.A., Huang M., Rice W.G., Appella E., and Inman J.K. Bioorg. Med. Chem. Lett. 12 (2002) 767-770
20. Chin-Hsien W.A.N.G. Synthesis (1981) 622
21. Mizuno T., Nishiguchi I., Okushi T., and Hirashima T. Tetrahedron Lett. 32 (1991) 6867-6868
22. Chen Y.S., Schuphan I., and Casida J.E. J. Agric. Food Chem. 27 (1979) 709-712
23. Rafin C., Veignie E., Sancholle M., Postel D., Len C., Villa P., and Ronco G. J. Agric. Food Chem. 48 (2000) 5283-5287
24. Len C., Postel D., Ronco G., Villa P., Goubert C., Jeufrault E., Mathon B., and Simon H. J. Agric. Food Chem. 45 (1997) 3-6
25. Morf P., Raimondi F., Nothofer H.-G., Schnyder B., Yasuda A., Wessels J.M., and Jung T.A. Langmuir 22 (2006) 658-663
26. McClain A., and Hsieh Y.-L. J. Appl. Polym. Sci. 92 (2004) 218-225
27. Dunn A.D., and Rudorf W.-D. Carbon Disulphide in Organic Chemistry (1989), Ellis Horwood, Chichester, UK pp 226-367
28. Nieuwenhuizen P.J., Ehlers A.W., Haasnoot J.G., Janse S.R., Reedijk J., and Baerends E.J. J. Am. Chem. Soc. 121 (1999) 163-168
29. Thorn G.D., and Ludwig R.A. The Dithiocarbamates and Related Compounds (1962), Elsevier, Amsterdam
30. Wood M.R., Duncalf D.J., Rannard S.P., and Perrier S. Org. Lett. 8 (2006) 553-556
31. Crich D., and Quintero L. Chem. Rev. 89 (1989) 1413-1432
32. Barton D.H.R. Tetrahedron 48 (1992) 2529-2544
33. Zard S.Z. Angew. Chem., Int. Ed. 36 (1997) 672-685
34. Zhang D., Chen J., Liang Y., and Zhou H. Synth. Commun. 35 (2005) 521-526
35. Tilles H. J. Am. Chem. Soc. 81 (1959) 714-727
36. Sugiyama H.J. Synth. Org. Chem. Jpn. 38 (1980) 555-563
37. Walter W., and Bode K.-D. Angew. Chem., Int. Ed. Engl. 6 (1967) 281-293
38. Azizi N., Aryanasab F., Torkiyan L., Ziyaei A., and Saidi M.R. J. Org. Chem. 71 (2006) 3634-3635
39. Azizi N., Pourhasan B., Aryanasab F., and Saidi M.R. Synlett (2007) 1239-1242
40. Azizi N., Ebrahimi F., Aakbari E., Aryanasab F., and Saidi M.R. Synlett (2007) 2797-2800
41. Azizi N., Pourhasan B., Aryanasab F., and Saidi M.R. Org. Lett. 8 (2006) 5275-5277
42. Bhadra S., Saha A., and Ranu B.C. Green Chem. 10 (2008) 1224-1230
43. Ranu B.C., Saha A., and Banerjee S. Eur. J. Org. Chem. (2008) 519-523
44. Liu Y., and Bao W. Tetrahedron Lett. 48 (2007) 4785-4788
45. Chaturvedi D., Mishra N., and Mishra V. J. Sulfur Chem. 28 (2007) 39-44
46. Chaturvedi D., and Ray S. Monatsh. Chem. 137 (2006) 311-317
47. Hayashi T. Tetrahedron Lett. 15 (1974) 339-342
48. Nakai T., Shiono H., and Okawara M. Tetrahedron Lett. 15 (1974) 3625-3628
49. Nakai T., Shiono H., and Okawara M. Chem. Lett. 4 (1975) 249-252
50. Hayashi T. Tetrahedron Lett. 31 (1990) 4155-4158
51. Chinchilla R., and Najera C. Chem. Rev. 100 (2000) 1891-1928
52. Bakuzis P., Bakuzis M.L.F., and Weingartner T.F. Tetrahedron Lett. 19 (1978) 2371-2374
53. In: ApSimon J. (Ed). The Total Synthesis of Natural Products Vol. 8 (1988), John Wiley, New York 102
54. Corey E.J., Erickson B.W., and Noyori R. J. Am. Chem. Soc. 93 (1971) 1724-1729
55. In: Bindra J.S., and Bindra R. (Eds). Prostaglandin Synthesis (1977), Academic Press, New York
56. de Montarby L., Tourbah H., and Gree R. Bull. Soc. Chim. Fr. 126 (1989) 419-431
57. Baylis, A. B.; Hillaman, M. E. D. Offenlegungsschrift 2155113, U.S. Patent 3,743,669, 1972; Chem. Abstr. 1972, 77, 34174.
58. In: Ciganek E. (Ed). Organic Reactions Vol. 51 (1997), Wiley, New York, NY 201-305
59. Singh V., and Batra S. Tetrahedron 64 (2008) 4511-4574
60. Basavaiah D., Rao K.V., and Reddy R.J. Chem. Soc. Rev. 36 (2007) 1581-1588
61. Basavaiah D., Rao A.J., and Satyanarayana T. Chem. Rev. 103 (2003) 811-891
62. Langer P. Angew. Chem., Int. Ed. 39 (2000) 3049-3052
63. Basavaiah D., Rao P.D., and Hyma R.S. Tetrahedron 52 (1996) 8001-8062
64. Basavaiah D., and Roy S. Org. Lett. 10 (2008) 1819-1822
65. Basavaiah D., Reddy K.R., and Kumaragurubaran N. Nat. Protoc. 2 (2007) 2665-2676
66. Basavaiah D., and Reddy R.J. Org. Biomol. Chem. 6 (2008) 1034-1039
67. Yadav J.S., Reddy B.V.S., Basak A.K., Narsaiah A.V., Prabhakar A., and Jagadeesh B. Tetrahedron Lett. 46 (2005) 639-641
68. Shafiq Z., Liu L., Liu Z., Wang D., and Chen Y.-J. Org. Lett. 9 (2007) 2525-2528
69. Reddy C.R., Kiranmai N., Babu G.S.K., Sarma G.D., Jagadeesh B., and Chandrasekhar S. Tetrahedron Lett. 48 (2007) 215-218
70. Ollevier T., and Mwene-Mbeja T.M. Tetrahedron 64 (2008) 5150-5155
71. Basavaiah D., and Satyanarayana T. Tetrahedron Lett. 43 (2002) 4301-4303
72. Yadav J.S., Gupta M.K., Pandey S.K., Reddy B.V.S., and Sarma A.V.S. Tetrahedron Lett. 46 (2005) 2761-2763
73. Li J., Wang X., and Zhang Y. Tetrahedron Lett. 46 (2005) 5233-5237
74. Paira M., Mandal S.K., and Roy S.C. Tetrahedron Lett. 49 (2008) 2432-2434
75. Kabalka G.W., Venkataiah B., and Dong G. Tetrahedron Lett. 44 (2003) 4673-4675
76. Liu Y., Xu D., Xu Z., and Zhang Y. Heteroat. Chem. 19 (2008) 188-198
77. Das B., Chowdhury N., Damodar K., and Banerjee J. Chem. Pharm. Bull. 55 (2007) 1274-1276
78. Cha M.J., Song Y.S., and Lee K.-J. Bull. Korean Chem. Soc. 27 (2006) 1900-1902
79. Kamimura A., Morita R., Matsuura K., Omata Y., and Shirai M. Tetrahedron Lett. 43 (2002) 6189-6191
80. Binay, P.; Henary, J. C.; Vidal, V.; Genet, J. P.; Dellis, P. Fr. Demande FR2772027, 1999, 23 p; Chem. Abstr. 1999, 131, 170171.
81. Deane P.O., Guthrie-Strachan J.J., Kaye P.T., and Whittaker R.E. Synth. Commun. 28 (1998) 2601-2611
82. Shrihari P., Singh A.P., Jain R., and Yadav J.S. Synthesis (2006) 2772-2776
83. Li C.-J., and Chan T.-H. Organic Reactions in Aqueous Media (1997), Wiley, New York
84. In: Grieco P.A. (Ed). Organic Synthesis in Water (1998), Blackie Academic and Professional, London
85. Lindstrom U.M. Chem. Rev. 102 (2002) 2751-2772
86. Li C.-J. Chem. Rev. 105 (2005) 3095-3166
87. Yadav L.D.S., Yadav S., and Rai V.K. Green Chem. 8 (2006) 455-458
88. Yadav L.D.S., Yadav B.S., and Rai V.K. Synthesis (2006) 1868-1872
89. Yadav L.D.S., Patel R., Rai V.K., and Srivastava V.P. Tetrahedron Lett. 48 (2007) 7793-7795
90. Yadav L.D.S., and Rai V.K. Synlett (2007) 1227-1230
91. Yadav L.D.S., Patel R., and Srivastava V.P. Synlett (2008) 1789-1792
92. Yadav L.D.S., Srivastava V.P., and Patel R. Tetrahedron Lett. 49 (2008) 5652-5654
93. Yadav L.D.S., Awasthi C., and Rai A. Tetrahedron Lett. 49 (2008) 6360-6363
94. 2: C, 63.83; H, 5.36; N, 3.92. Found: C, 63.60; H, 5.25; N, 3.55.
95. Basavaiah D., Sarma P.K.S., and Bhavani A.K.D. J. Chem. Soc., Chem. Commun. (1994) 1091-1092
96. Minami I., Yuhara M., Shimizu I., and Tsuji J. J. Chem. Soc., Chem. Commun. (1986) 118-119
97. Buchholz R., and Hoffmann H.M.R. Helv. Chim. Acta 74 (1991) 1213-1220
98. Das B., Banerjee J., and Ravindranath N. Tetrahedron 60 (2004) 8357-8361
99. 2: C, 66.63; H, 4.97; N, 8.63. Found: C, 66.97; H, 4.74; N, 8.46.