Triton-B-catalyzed, efficient, one-pot synthesis of carbazates through alcoholic tosylates

Synthetic Communications

Volumn 38, Issue 22, 2008, Pages 4013-4022

  Chaturvedi, Devdutt ^a   Chaturvedi, Amit K ^b   Mishra, Nisha ^b   Mishra, Virendra ^b  

^a CSIR INDIAN INSTITUTE OF INTEGRATIVE MEDICINE   (India)

^b B S A P G College   (India)

Author keywords

Alcoholic tosylates; Benzyltrimethylammonium hydroxide; Carbazates; Carbon dioxide; Substituted hydrazines

Indexed keywords

ALCOHOL; AMMONIUM HYDROXIDE; BENZYLTRIMETHYLAMMONIUM HYDROXIDE; CARBAZIC ACID DERIVATIVE; HYDRAZINE DERIVATIVE; TOLUENESULFONIC ACID DERIVATIVE; TYLOXAPOL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; ONE POT SYNTHESIS;

EID: 54349121353     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802269259     Document Type: Article

References (33)

1. (a) Bharti, N.; Maurya, M. R.; Naqvi, F.; Azam, A. Synthesis and antiamoebic activity of new cyclo-octadiene ruthenium(II) complexes with 2-acetylpyridine and benzimidazole derivatives. Bio-Org. Med. Chem. Lett. 2000, 10, 2243-2245;
2. (b) Bharti, N.; Mannar, M. R.; Fehmida, N.; Bhattacharya, A.; Bhattacharya, S.; Azam, A. Palladium(II) complexes of NS donor ligend derived from S-methyl dithiocarbazate, S-benzyl dithiocarbazate, thiosemicarbazide as anti-amoebic agents. Eur. J. Med. Chem. 2000, 35, 481-486.
3. Sengupta, S.; Pandey, O. P.; Rao, G. P. Sugarcane Pathol.: Fungal Dis., 1999, 1, 279-302.
4. (a) Connolly, T. J.; Crittal, A. J.; Ebrahim, A. S.; Ji, G. Development and scale up of a route to cyclohecylhydrazine dimethanesulfonate. Org. Process. Res. Dev. 2000, 4, 526-529;
5. (b) Gordan, M. S.; Krause, J. G.; Linneman-Mohr, M. A.; Parchue, R. R. Hydrazides and hydrazones from carbazates. Synthesis 1980, 3, 244-246;
6. (c) Hauser, M. J. The preparation and cyclization of some chloroethyl carbazates: Some clarifications. J. Org. Chem. 1966, 31, 968-970.
7. Wuts, P. G. M.; Greene, T. W. Greene's Protective Groups in Organic Synthesis, John Wiley Interscience, Chichester, UK, 2006, 706-887.
8. (a) Huang, J. Y.; Choi, H. S.; Lee, D. H.; Yoo, S. E.; Gong, Y. D. Solid phase synthesis of 5-amino-1-(substituted thiocarbomyl)pyrazole and 1,2,4-triazole derivatives via dithiocarbazate linker. J. Comb. Chem. 2005, 7, 136-141;
9. (b) Hwang, J. Y.; Choi, H. S.; Lee, D. H.; Gong, Y. D. Solid phase synthesis of 1,3,4-oxadiazole and 1,3,4-thiadiazole derivatives via selective reagent based cyclization of acyldithiocarbazate resins. J. Comb. Chem. 2005, 7, 816-819.
10. 99mTC compounds as potential brain imaging agents. Bioconjugate Chem., 2006, 17, 419-428;
11. (b) Ali, M. A.; Mirza, A. H.; Butcher, R. J.; Krause, K. A. The preparation, characterization, and biological activity of palladium(II) and platinum(II) complexes of tridentate NNS ligends derived from S-methyl and S-benzyldithiocarbazates and X-ray crystal structure of the [Pd(mpasme)cl] complexes. Transition Met. Chem. 2006, 31, 79-87.
12. Dyker, H.; Scherkenbeck, J.; Gondol, D.; Goehrt, A.; Harder, A. Azadepsipetides: Synthesis and evaluation of a novel class of peptidomimetics. J. Org. Chem. 2001, 66, 3760-3766.
13. Nara, S.; Sakamoto, T.; Miyazawa, E.; Kikugawa, Y. A convenient synthesis of 1-alkyl 1-phenylhydrazines from 1-aminopthalimide. Synth. Commun. 2003, 33, 87-98.
14. 3 and TBAI. Tetrahedron Lett. 2004, 45, 401-405.
15. For Reviews, see (a) Chaturvedi, D.; Ray, S. Versatile use of carbon dioxide in the synthesis of organic carbamates. Curr. Org. Chem. 2007, 11, 987-998;
16. (b) Chaturvedi, D.; Misra, N.; Mishra, V. Various approaches for the synthesis of organic carbamates. Curr. Org. Synth. 2007, 3, 308-320;
17. For research work, see (c) Chaturvedi, D.; Kumar, A.; Ray, S. An efficient, one-pot synthesis of carbamate esters through alcoholic tosylates. Synth Commun. 2002, 32, 2651-2655;
18. (d) Chaturvedi, D.; Kumar, A.; Ray, S. A high yielding, one-pot novel synthesis of carbamate esters from corresponding alcohols using Mitsunobu's reagent. Tetrahedron Lett. 2003, 44, 7637-7639;
19. (e) Chaturvedi, D.; Ray, S. An efficient, one-pot, basic resin catalyzed, novel synthesis of carbamate esters through alcoholic tosylayes. Lett. Org. Chem. 2005, 2, 742-744;
20. (f) Chaturvedi, D.; Ray, S. An efficient, basic resin mediated, one-pot synthesis of dithiocarbamate esters through alcoholic tosylates. J. Sulfur Chem. 2005, 26, 365-371;
21. (g) Chaturvedi, D.; Ray, S. An efficient, basic resin mediated, one-pot synthesis of O-alkyl S-methyl dithiocarbonates from the corresponding alcohols. J. Sulfur Chem. 2006, 27, 265-271;
22. (h) Chaturvedi, D.; Ray, S. An efficient, one-pot synthesis of dithiocarbamates from the corresponding alcohols using Mitsunobu's reagent. Tetrahedron Lett. 2006, 47, 1307-1309;
23. (i) Chaturvedi, D.; Mishra, N.; Mishra, V. An efficient and novel synthesis of carbamate esters from the coupling of amines, halides, and carbon dioxide in the presence of basic resin. Chin. Chem. Lett. 2006, 17, 1309-1312;
24. (j) Chaturvedi, D.; Ray, S. A high yielding, one-pot synthesis of O,S-dialkyl dithiocarbonates from alcohols using Mitsunobu's reagent. Tetrahedron Lett. 2007, 48, 149-151;
25. (k) Chaturvedi, D.; Mishra, N.; Mishra, V. An efficient, basic resin mediated, one-pot synthesis of dithiocarbamates by Michael addition of dithiocarbamate to activated olefins. J. Sulfur Chem. 2007, 28, 39-44;
26. (l) Chaturvedi, D.; Mishra, N.; Mishra, V. A high yielding, one-pot synthesis of dialkylcarbonates from alcohols using Mitsunobu's reagent. Tetrahedron Lett. 2007, 48, 5043-5045;
27. (m) Chaturvedi, D.; Mishra, N.; Mishra, V. An efficient, one-pot synthesis of S-alkyl thiocarbamates from the corresponding thiols using Mitsunobu's reagent. Synthesis 2008, 355-357.
28. (a) Chaturvedi, D.; Ray, S. A high yielding, one-pot Triton-B catalyzed expeditious synthesis of carbamate esters through four component coupling methodology. Monatsh. Chem. 2006, 137, 201-206;
29. (b) Chaturvedi, D.; Ray, S. Triton-B catalyzed efficient, one-pot synthesis of dithiocarbamate esters. Monatsh. Chem. 2006, 137, 311-317;
30. (c) Chaturvedi, D.; Ray, S. Triton-B catalyzed, efficient, one-pot synthesis of carbamate esters from alcoholic tosylates. Monatsh. Chem. 2006, 137, 459-463;
31. (d) Chaturvedi, D.; Ray, S. A high yielding, one-pot synthesis of dithiocarbamates using alcoholic tosylates. Monatsh. Chem. 2006, 137, 465-459;
32. (e) Chaturvedi, D.; Ray, S. An efficient, one-pot Triton-B catalyzed synthesis of O-alkyl S-methyl dithiocarbonates. Monatsh. Chem. 2006, 137, 1219-1223.
33. Kabalka, G. W.; Varma, M.; Varma, R. S.; Srivastava, P. C.; Knapp, F. F. Tosylation of alcohols. J. Org. Chem. 1986, 51, 2386-2388.