New synthesis of 2,3-disubstituted and 2,2,3-trisubstituted 2H-1- benzothiopyran derivatives

Tetrahedron Letters

Volumn 37, Issue 29, 1996, Pages 5077-5080

  Gauthier, Sylvain ^a   Labrie, Fernand ^a  

^a LAVAL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID DERIVATIVE; BENZOTHIOPYRAN DERIVATIVE; THIOPYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CYCLIZATION; DRUG SYNTHESIS; ISOMER; NUCLEAR OVERHAUSER EFFECT; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REDUCTION;

EID: 0030586167     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01069-6     Document Type: Article

References (11)

1. (1) Tércio, J.; Ferreira, B.; Catani, V.; Comasseto, J.V. Synthesis 1987, 149. Camps, F.; Colomina, O.; Coll, J.; Messeguer, A. J. Heterocyclic Chem. 1983, 20, 1115.
2. (1) Tércio, J.; Ferreira, B.; Catani, V.; Comasseto, J.V. Synthesis 1987, 149. Camps, F.; Colomina, O.; Coll, J.; Messeguer, A. J. Heterocyclic Chem. 1983, 20, 1115.
3. (2) Schneller, S.W. Adv. Heterocyclic Chem. 1975, 18, 59. Katekar, G.F.; Thomson, R.M. Aust. J. Chem. 1972, 25, 647. Collins, D.J.; Hobbs, J.J. Aust. J. Chem. 1974, 27, 1545.
4. (2) Schneller, S.W. Adv. Heterocyclic Chem. 1975, 18, 59. Katekar, G.F.; Thomson, R.M. Aust. J. Chem. 1972, 25, 647. Collins, D.J.; Hobbs, J.J. Aust. J. Chem. 1974, 27, 1545.
5. (2) Schneller, S.W. Adv. Heterocyclic Chem. 1975, 18, 59. Katekar, G.F.; Thomson, R.M. Aust. J. Chem. 1972, 25, 647. Collins, D.J.; Hobbs, J.J. Aust. J. Chem. 1974, 27, 1545.
6. (3) Arnoldi, A.; Carughi, M. Synthesis 1988, 155.
7. (4) Meth-Cohn, O.; Tarnowski, B. Synthesis 1978, 56.
8. (5) (E,Z)-α,β-Unsaturated ketones 2 could be separated by Chromatography. The stereochemistry of the double bond of α,β-unsaturated ketones 2 was determined via the NOE experiments. Irradiation of the vinyl proton of compounds 2a-d showed a NOE with the benzoyl (ortho) protons (2a,b) or the methylene protons (2c,d) and thus, the (E)-isomer of ketones 2 was assigned.
9. 1H NMR spectra, the crude contains a (2:3) mixture of the starting (E)-allylic alcohol 3d and the corresponding (E)-allylic trifluoroacetate 6d.
10. (7) The low temperature experiments suggest the increasing order of reactivity of the (E,Z)-allylic alcohols 3 as follows: 3c < 3d ≪ 3a < 3b.
11. (8) The attack at the α-position gives benzothiete derivatives which were not observed.