New Applications of 2,4,6-Trichloro-1,3,5-triazine (TT) in Synthesis: Highly Efficient and Chemoselective Deprotection and Ring-Enlargement of Dithioacetals and Oxathioacetals

Babak Karimi; Hassan Hazarkhani

doi:10.1055/s-2003-42459

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Synthesis 2003(16): 2547-2551
DOI: 10.1055/s-2003-42459

PAPER

New Applications of 2,4,6-Trichloro-1,3,5-triazine (TT) in Synthesis: Highly Efficient and Chemoselective Deprotection and Ring-Enlargement of Dithioacetals and Oxathioacetals

Babak Karimi*, Hassan Hazarkhani
Department of Chemistry, Institute for Advanced Studies in Basic Sciences (IASBS), P.O. Box 45195-159, Gava Zang, Zanjan, Iran
Fax: +98(241)4249023; e-Mail: Karimi@iasbs.ac.ir;

Further Information

Publication History

Received 24 March 2003
Publication Date:
06 November 2003 (online)

Abstract
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Abstract

Efficient deprotection of a wide variety of 1,3-dithioacetals and 1,3-oxathiolanes to the corresponding carbonyl compounds at room temperature using a combination of 2,4,6-trichloro-1,3,5-triazine (TT) and dimethyl sulfoxide (DMSO) was investigated. In this way, 1,3-oxathioacetals and 1,3-dithioacetals of enolizable ketones were converted to the corresponding 1,4-oxathiepine and 1,4-dithiepine derivatives, respectively.

Key words

chemoselective - 1,3-dithioacetals - 1,3-oxathiolanes - carbonyl compounds

References

1a Greene TW. Wuts PGM. Protective Groups in Organic Synthesis 3rd ed.: Wiley; New York: 1999.

Google Scholar
1b Kocienski PJ. Protecting Groups Thieme; New York: 1994.

Google Scholar
2a Fuji K. Ueda M. Fujita E. J. Chem. Soc., Chem. Commun. 1977, 814

Crossref Google Scholar
2b Fuji K. Ueda M. Sumi K. Kajiwara K. Fujita E. Iwashita T. Miura I. J. Org. Chem. 1985, 50: 657

Crossref Google Scholar
2c Fuji K. Ueda M. Sumi K. Fujita E. Tetrahedron Lett. 1981, 22: 2005

Crossref Google Scholar
2d Fuji K. Ueda M. Fujita E. J. Chem. Soc., Chem. Commun. 1983, 49

Crossref Google Scholar
3a Lynch JE. Eliel EL. J. Am. Chem. Soc. 1984, 106: 2943

Google Scholar
3b Eliel EL. Morris-Natschke S. J. Am. Chem. Soc. 1984, 106: 2937

Google Scholar
3c Frye SV. Eliel EL. Tetrahedron Lett. 1985, 26: 3907

Google Scholar
3d Eliel EL. Soai K. Tetrahedron Lett. 1981, 21: 2859

Google Scholar
4a Isobe M. Obeyama J. Funabashi Y. Goto T. Tetrahedron Lett. 1988, 29: 4773

Crossref Google Scholar
4b Utimoto K. Nakamura A. Matsubara S. J. Am. Chem. Soc. 1990, 112: 8189

Crossref Google Scholar
5a Degani I. Fochi R. Regondi V. Synthesis 1981, 51

Google Scholar
5b Fujita E. Nagao Y. Kanero K. Chem. Pharm. Bull. 1978, 26: 3743

Google Scholar
6a Ghringhelli D. Synthesis 1982, 580

Crossref Google Scholar
6b Liu HJ. Winszniewski V. Tetrahedron Lett. 1988, 29: 5471

Crossref Google Scholar
7 Ho TL. Ho HC. Wong CM. J. Chem. Soc., Chem. Commun. 1972, 791

Google Scholar
8 Haroutounian SA. Synthesis 1995, 39

Article in Thieme Connect Google Scholar
9a Rotermund GW. Houben-Weyl, Methoden der Organischen Chemie Vol. 4/1b: Müller E. Thieme; Stuttgart: 1975. p.407

Crossref Google Scholar
9b Ho TL. Wong CM. Can. J. Chem. 1972, 50: 3740

Crossref Google Scholar
10a Mehta G. Uma R. Tetrahedron Lett. 1996, 37: 1879

Crossref Google Scholar
10b Oishi T. Kamemoto K. Ban Y. Tetrahedron Lett. 1972, 11: 1085

Crossref Google Scholar
10c Fetizon M. Jurion M. J. Chem. Soc., Chem. Commun. 1977, 680

Crossref Google Scholar
11a Komatsu N. Tanguchi A. Uda M. Suzuki H. Chem. Commun. 1996, 1847

Crossref Google Scholar
11b Balogh M. Cornelis A. Laszlo P. Tetrahedron Lett. 1984, 25: 3313

Crossref Google Scholar
11c Stork G. Zhao K. Tetrahedron Lett. 1989, 30: 287

Crossref Google Scholar
11d Tanemura K. Dohya H. Imamura M. Suzuki T. Horaguchi T. J. Chem. Soc., Perkin Trans. 1 1996, 453

Crossref Google Scholar
11e Firouzabadi H. Iranpoor N. Hazarkhani H. Karimi B. J. Org. Chem. 2002, 67: 2572 ; and references cited therein

Crossref Google Scholar
11f Curini M. Marcotullio MC. Pisani E. Rosati O. Synlett 1997, 769

Crossref Google Scholar
11g Bandgar BP. Kasture SP. Green Chem. 2000, 2: 154

Crossref Google Scholar
12a Fuji K. Ichikawa K. Fujita E. Tetrahedron Lett. 1978, 3561

Crossref Google Scholar
12b Emerson DW. Wynberg H. Tetrahedron Lett. 1971, 3445

Crossref Google Scholar
13 Ravindranathan T. Chavan SP. Dantale SW. Tetrahedron Lett. 1995, 36: 2285

Google Scholar
14a Ravindranathan T. Chavan SP. Tejwani RB. Varghese JP. J. Chem. Soc., Chem. Commun. 1991, 1750

Crossref Google Scholar
14b Ravindranathan T. Chavan SP. Varghese JP. Dantale SW. Tejwani RB. J. Chem. Soc., Chem. Commun. 1994, 1937

Crossref Google Scholar
15 Ravindranathan T. Chavan SP. Awachat MM. Tetrahedron Lett. 1994, 35: 8835

Crossref Google Scholar
16a Nishide K. Yokota K. Nakamura D. Sumiya T. Node M. Ueda M. Fuji K. Tetrahedron Lett. 1993, 34: 3425

Google Scholar
16b Nishide K. Yokota K. Nakamura D. Sumiya T. Node M. Ueda M. Fuji K. Heterocycles 1997, 44: 393

Google Scholar
17 Karimi B. Seradj H. Tabaei MH. Synlett 2000, 1798

Article in Thieme Connect Google Scholar
18 Mondal E. Sahu PR. Bose G. Khan AT. Tetrahedron Lett. 2002, 43: 2843

Crossref Google Scholar
19 Kirihara M. Ochiai Y. Aria N. Takizawa S. Momose T. Nemoto H. Tetrahedron Lett. 1999, 40: 9055

Crossref Google Scholar
20 Senier A. Ber. Dtsch. Chem. Ges. 1886, 19: 311

Google Scholar
21 Venkataraman K. Wagle DR. Tetrahedrom Lett. 1979, 3037

Google Scholar
22 Venkataraman K. Wagle DR. Tetrahedron Lett. 1980, 21: 1893

Crossref Google Scholar
23 Falorni M. Porcheddu A. Taddei M. Tetrahedron Lett. 1999, 40: 4395

Crossref Google Scholar
24 Forbes DC. Barrett EJ. Lewis DL. Smith MC. Tetrahedron Lett. 2000, 41: 9943

Crossref Google Scholar
25 Manhas MS. Bose AK. Khajavi MS. Synthesis 1981, 209

Article in Thieme Connect Google Scholar
26 Olah GA. Fung AP. Gupta BGB. Narang SC. Synthesis 1980, 221

Article in Thieme Connect Google Scholar
27 De Luca L. Giacomelli G. Porcheddu A. J. Org. Chem. 2002, 67: 5152

Crossref Google Scholar
28 De Luca L. Giacomelli G. Porcheddu A. J. Org. Chem. 2001, 66: 7907

Crossref Google Scholar
29 De Luca L. Giacomelli G. Porcheddu A. Org. Lett. 2002, 4: 553 ; and references cited therein

Crossref Google Scholar
30 Karimi B. Hazarkhani H. Zareyee D. Synthesis 2002, 2513

Article in Thieme Connect Google Scholar
31 Firouzabadi H. Iranpoor N. Karimi B. Synlett 1999, 413

Article in Thieme Connect Google Scholar
32 Crenova Inc.; XX Z. Org. Proc. Res. Dev. 2002, 6: 354

Google Scholar
33a Chen CH. Tetrahedron Lett. 1976, 25

Google Scholar
33b Chen CH. Donatelli BA. J. Org. Chem. 1976, 41: 3053

Google Scholar
33c Janssen JWAM. Kwart H. J. Org. Chem. 1977, 42: 1530

Google Scholar
33d Bulman-Page PC. Ley SV. Morton JA. J. Chem. Soc., Perkin Trans. 1 1981, 457

Google Scholar
33e Francisco CG. Freire R. Hernandez R. Salazar JA. Suarez E. Tetrahedron Lett. 1984, 25: 1621

Google Scholar
33f Tani H. Inamasu T. Tamura R. Suzuki H. Chem. Lett. 1990, 1323

Google Scholar
33g Tani H. Inamasu T. Masumoto K. Tamura R. Shimizu H. Suzuki H. Phosphorus, Sulfur Silicon Relat. Elem. 1992, 67: 261

Google Scholar