Stereoselective synthesis of 2,4-disubstituted thiochromans using the supported reagent system 'Na2CO3/SiO2-PPA/ SiO2'

Synlett

Volumn , Issue 3, 2007, Pages 387-390

  Aoyama, Tadashi ^a   Okada, Kazuyuki ^a   Nakajima, Hideaki ^a   Matsumoto, Takuo ^b   Takido, Toshio ^a   Kodomari, Mitsuo ^c  

^a NIHON UNIVERSITY   (Japan)

^b DAIICHI SANKYO CO   (Japan)

^c SHIBAURA INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Stereoselective synthesis; Supported reagents; Thiochroman

Indexed keywords

ALDEHYDE; POLYPHOSPHATE; REAGENT; SILICON DIOXIDE; SODIUM CARBONATE; THIOCHROMAN DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; MICHAEL ADDITION; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 33847342479     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-967935     Document Type: Article

References (14)

1. Advances in Heterocyclic Chemistry, Vol. 18; Katrizky, A. R.; Boulton, A. J., Eds.; Academic Press: New York, 1975, 76.
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3. Nakazawa, T.; Sato, K.; Itabashi, K. Nihon Kagaku Kaishi 1990, 119.
4. Jafarzadeh, M.; Amani, K.; Nikpour, F. Tetrahedron Lett. 2005, 46, 7567.
5. Ishino, Y.; Mihara, M.; Kawai, H. Synlett 2001, 1317.
6. Aoyama, T.; Takido, T.; Kodomari, M. Synlett 2004, 2307.
7. Aoyama, T.; Takido, T.; Kodomari, M. Synlett 2005, 2739.
8. (a) Mckillop, A.; Young, D. W. Synthesis 1979, 401.
9. (b) Posner, G. H. Angew. Chem., Int. Ed. Engl. 1978, 17, 487.
10. (c) Cornelis, A.; Laszlo, P. Synthesis 1985, 909.
11. 3 was removed with rotary evaporator and the resulting solid was dried in vacuo (10 mmHg) at r.t. for 3 h.
12. 2O was removed by rotary evaporator under reduced pressure, and the resulting reagent was dried in vacuo (10 mmHg) at 160°C for 5 h.
13. 2 (20 wt%, 3.00 g) was stirred in PhCl (15 mL) at 80°C for 4 h, and then the used supported reagents were removed by filtration. The filtrate was evaporated to leave crude product, which was purified by column chromatography eluted with hexane-EtOAc (300:1).
14. 3): δ = 1.33 (3 H, s), 1.38 (3 H, s), 2.14-2.25 (2 H, m), 2.30 (3 H, s), 2.33 (3 H, s), 4.42 (1 H, dd, J = 10.0, 6.4 Hz), 6.92-6.99 (2 H, m), 7.09 (2 H, d, J = 7.8 Hz), 7.26-7.29 (2 H, m), 7.65 (1 H, s).