Palladium-mediated synthesis of 5-substituted 4-alkynylthieno[2,3-c]pyran- 7-ones

Tetrahedron Letters

Volumn 47, Issue 1, 2006, Pages 83-88

  Raju, Sirisilla ^a,b   Batchu, Venkateswara Rao ^a   Swamy, Nalivela Kumara ^a   Vasu Dev, R ^a   Babu, J Moses ^a   Rajender Kumar, P ^a   Mukkanti, K ^b   Pal, Manojit ^a  

^a DR REDDY'S LABORATORIES LTD   (India)

^b JAWAHARLAL NEHRU TECHNOLOGICAL UNIVERSITY   (India)

Author keywords

3 Iodothiophene 2 carboxylic acid; 4 Alkynylthieno 2,3 c pyran 7 one; Palladium catalyst; Terminal alkynes

Indexed keywords

3 IODOTHIOPHENE 2 CARBOXYLIC ACID; ALKYNE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; PALLADIUM; PYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 28544436329     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.10.135     Document Type: Article

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31. Single crystals suitable for X-ray diffraction of 2b were grown from chloroform. Crystals were obtained as colourless plates in the triclinic space group PĪ with cell dimensions a = 7.565 (2), b = 7.938 (1), c = 11.083 (2), α = 98.525 (3), β = 105.020 (6), γ = 101.606 (6) and V = 615.4 (2) containing 2 molecules in the unit cell. The intensity data have been collected on a Rigaku AFC-7S single crystal diffractometer using Mo Kα (λ = 0.7107 Å). The structure was solved by direct methods, and was refined using least squares procedures using the Crystal Structure software. The present R factors of 2b are: R (Rw) = 0.099 (0.15, with 1687 reflections). Crystallographic data (excluding structure factors) for 2b have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 280767.
32. 3, 50 MHz) 157.9 (CO), 156.9, 154.5, 153.8, 152.7, 137.0, 129.6 (2C), 129.5 (2C), 126.6, 124.7, 121.8, 121.7, 115.0 (2C), 114.9 (2C), 101.2, 92.7, 78.1, 65.0, 56.2; UV (nm, MeOH) 313.0, 255.8, 202.8; HPLC 97.0%, column: Zorbax Eclipse XDB C-18 (150 × 4.6) mm, mobile phase A: 0.05% TFA in water, mobile phase B: 0.05% TFA in methanol, gradient (T/%B): 0/30, 13/70, 15/100, 25/100, flow rate 1.0 mL/min, UV 254 nm, retention time 17.4 min.
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