Convenient 'one-pot' synthesis of 3,4-substituted tetrahydrothiophenes through tandem Michael-Henry and Michael-Michael reactions

Tetrahedron Letters

Volumn 47, Issue 46, 2006, Pages 8087-8090

  Barco, Achille ^a   Baricordi, Nikla ^a   Benetti, Simonetta ^a   De Risi, Carmela ^b   Pollini, Gian Piero ^b  

^a Dipartimento di Chimica   (Italy)

^b Dipto di Scienze Farmaceutiche   (Italy)

Author keywords

Henry reactions; Michael reactions; Tandem reactions; Tetrahydrothiophenes

Indexed keywords

1,4 DITHIANE 2,5 DIOL; 4 MERCAPTO 2 BUTENOATE DERIVATIVE; ACETALDEHYDE; ALKENE DERIVATIVE; DIMER; MERCAPTOACETALDEHYDE; TETRAHYDROTHIOPHENE DERIVATIVE; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; MICHAEL ADDITION; SUBSTITUTION REACTION;

EID: 33749526830     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.09.055     Document Type: Article

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16. 6): δ 2.72-2.89 (m, 1H), 3.05-3.12 (dd, 1H, J = 11.2, 6.2 Hz), 3.18-3.22 (m, 1H), 3.38 (dd, 1H, J = 10.3, 3.7 Hz), 5.05 (m, 1H), 5.18-5.22 (m, 1H).
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19. A synthesis of thiolanes via consecutive Michael additions has been reported previously using methyl 4-mercaptocrotonate formed photochemically from dihydro-2(5H)-thiophenone:. Anklam E., and Margaretha P. Helv. Chim. Acta 67 (1984) 2206-2209
20. 3): δ 1.28 (t, 3H, J = 7.1 Hz), 2.52-2.59 (m, 2H), 2.74 (dd, 1H, J = 11.2, 6.2 Hz), 3.18-3.27 (m, 1H), 3.28-3.35 (m, 1H), 3.38 (dd, 1H, J = 10.3, 3.7 Hz), 3.54 (dd, 1H, J = 12.2, 5.8 Hz), 4.25-4.15 (q, 2H, J = 7.1 Hz), 4.92 (dd, 1H, J = 12.5, 6.1 Hz).