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Synlett 2016; 27(20): 2831-2835
DOI: 10.1055/s-0036-1589286
DOI: 10.1055/s-0036-1589286
letter
Efficient Synthesis of Spirooxindole-Fused 3-Thiazoline Derivatives by a One-Pot Asinger-Type Reaction
Weitere Informationen
Publikationsverlauf
Received: 07. Juli 2016
Accepted after revision: 27. August 2016
Publikationsdatum:
12. September 2016 (online)
![](https://www.thieme-connect.de/media/synlett/201620/lookinside/thumbnails/st-2016-d0440-l_10-1055_s-0036-1589286-1.jpg)
Abstract
A one-pot, three-component reaction has been developed and successfully employed for the synthesis of biologically relevant, highly functionalized spirooxindole-fused 3-thiazoline derivatives. Starting from ammonia, three mercapto carbonyl components and a series of substituted isatins, products were obtained in good yields (24 examples), by following a simple and rapid protocol. The obtained thiazolines proved to be optimal substrates for further transformations, including the three-component Ugi–Joullié reaction.
Key words
thiazoline - oxindole - spiro compounds - Asinger - multicomponent reactions - Ugi–Joullié reactionSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1589286.
- Supporting Information
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- 22 Synthesis of Spirooxindole-Fused 3-Thiazoline Derivatives 3a–x; General Procedure A (GP-A): To a solution of isatin 1a–r (1 mmol) in anhydrous toluene (1 mL, 1.0 M), MgSO4 (3 mmol) and NH3 (2 M in methanol, 2 mmol) were added. The solution was stirred for 8 h at r.t., then mercapto-derivative 2a–c was added (1.1 mmol). The resulting mixture was stirred for 30 min at the same temperature then diluted with CH2Cl2 (5 mL) and the solvent was removed under reduced pressure. The crude product was purified by flash chromatography (FC). Representative Analytical Data for 1-Benzyl-4′-methyl-5′H-spiro[indoline-3,2′-thiazol]-2-one (3a): Prepared according to GP-A using isatin 1a and mercaptoacetone 2a and purified by column chromatography (CH2Cl2–EtOAc, 19:1). Yield: 271 mg (88%); pale-orange foam. 1H NMR (300 MHz, CDCl3): δ = 7.36–7.24 (m, 6 H), 7.19 (br t, J = 7.7 Hz, 1 H), 7.04 (br t, J = 7.7 Hz, 1 H), 6.69 (br d, J = 7.8 Hz, 1 H), 4.94 (d, J = 15.7 Hz, 1 H), 4.84 (d, J = 15.7 Hz, 1 H), 4.43 (d, J = 15.8 Hz, 1 H), 4.27 (d, J = 15.8 Hz, 1 H), 2.32 (s, 3 H). 13C NMR (101 MHz, CDCl3): δ = 175.3, 174.9, 142.4, 135.4, 130.2, 129.6, 128.9 (2C), 127.7, 127.3 (2C), 125.5, 123.5, 109.5, 88.2, 48.7, 44.2, 19.9. HRMS (ESI): m/z [M + Na]+ calcd for C18H16N2NaOS+: 331.0876; found: 331.0884.