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Tandem hetero-Diels–Alder-hemiacetal reaction in the synthesis of new chromeno[4′,3′:4,5]thiopyrano[2,3-d]thiazoles

  • Andrii Lozynskyi , Vasyl Matiychuk , Olexandr Karpenko , Andrzej K. Gzella and Roman Lesyk EMAIL logo
Published/Copyright: January 28, 2017
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Heterocyclic Communications
From the journal Heterocyclic Communications Volume 23 Issue 1

Abstract

Novel rel-(5aR,6R,11bS)-6-hydroxy-3,5a,6,11b-tetrahydro-2H,5H-chromeno[4′,3′:4,5]thiopyrano[2,3-d][1,3]thiazole-2-ones were synthesized via tandem hetero-Diels-Alder-hemiacetal reaction of 5-(2-hydroxybenzylidene)-4-thioxo-2-thiazolidinones and α,β-unsaturated aldehydes. The stereochemistry of cycloadditions was confirmed by NMR spectra and a single crystal X-ray diffraction analysis.

Keywords: hetero-Diels-Alder-hemiacetal reaction; tandem reactions; thiopyrano[2,3-d][1,3]thiazoles; 4-thioxo-2-thiazolidinones; X-ray analysis

Introduction

The hetero-Diels–Alder reaction has been recognized as one of the most powerful and atom-economical protocols for construction of heterocyclic compounds. Over the past decades, numerous studies have been presented involving LUMO-lowering activation of electron deficient dienophiles in the synthesis of various thiopyran derivatives [1]. Examples of this methodology are the reactions of 5-methylidene-4-thioxo-2-thiazolidinone with different dienophiles including acrylonitrile [2], acrylic acid and its analogs [3], [4], [5], [6], [7], maleic and fumaric acids derivatives [8], [9], [10], [11], nitrostyrene [12], [13], arylidene pyruvic [14] and cinnamic acids derivatives [15], [16], 2(5H)furanone [17] and norbornene derivatives [18], [19], [20], [21]. α,β-Unsaturated aldehydes have been also reported as dienophiles in this reaction [2], [22].

Recently, we have reported that the reaction of 5-arylidene-4-thioxo-2-thiazolidinones with ortho-phenolic group at arylidene moiety with α,β-unsaturated carboxylic acid derivatives proceeds as diastereoselective tandem acylation-hetero-Diels-Alder reaction providing the 2H,5H-chromeno[4′,3′:4,5]thiopyrano[2,3-d]thiazoles (Scheme 1). Derivatives of maleic, fumaric [24], acrylic, crotonic, cynnamic [16] and itaconic [7] acids as well as 2(5H)furanone [17] have been studied as dienophiles in such type of heterodiene condensation. We have also established that the reaction of β,γ-unsaturated α-ketoacids with 5-(2-hydroxybenzylidene)-4-thioxo-2-thiazolidinones proceeds similarly as a tandem process with the pyran ring formation via the hemiacetal reaction yielding 6-hydroxy-2-oxo-5-phenyl-3,5a,6,11b-tetrahydro-2H,5H-chromeno[4′,3′:4,5]thiopyrano[2,3-d][1,3]thiazole-6-carboxylic acids. We have observed that the use of arylidene pyruvic acids in the hetero-Diels–Alder-hemiacetal reaction gives rise to a mixture of rel-(5S,5aR,11bR)- and rel-(5R,5aS,11bR)-annulated diastereoisomers [23].

Scheme 1 Recent results in the synthesis of chromenothiopyranothiazoles via tandem hetero-Diels-Alder reaction.
Scheme 1

Recent results in the synthesis of chromenothiopyranothiazoles via tandem hetero-Diels-Alder reaction.

Results and discussion

Following our previous results we applied α,β-unsaturated aldehydes as dienophiles in hetero-Diels–Alder reactions for the synthesis of novel fused thiopyrano[2,3-d]thiazole derivatives. The reaction of 5-(2-hydroxybenzylidene)-4-thioxo-2-thiazolidinones 1a–d and α,β-unsaturated aldehydes (acrolein, crotonaldehyde, trans-cinnamaldehyde) in boiling acetic acid afforded pure tetracyclic fused 6-hydroxy-3,5a,6,11b-tetrahydro-2H,5H-chromeno[4′,3′:4,5]thiopyrano[2,3-d][1,3]thiazole-2-ones 2a–l. Formation of the mixture of rel-(5aR,6R,11bS)- 2a–d and rel-(5S,5aR,6R,11bS)-annulated 2e–l diastereoisomers is regioselective and diastereoselective based on the use of α,β-unsaturated aldehydes followed by the hetero-Diels–Alder-hemiacetal tandem process (Scheme 2).

Scheme 2 Synthesis of rel-(5aR,6R,11bS)-6-hydroxy-3,5a,6,11b-tetrahydro-2H,5H-chromeno[4′,3′:4,5]thiopyrano[2,3-d][1,3]thiazole-2-ones 2a–l.
Scheme 2

Synthesis of rel-(5aR,6R,11bS)-6-hydroxy-3,5a,6,11b-tetrahydro-2H,5H-chromeno[4′,3′:4,5]thiopyrano[2,3-d][1,3]thiazole-2-ones 2a–l.

The structures and stereochemical features of final products were established by analysis of the 1H NMR spectra. Thus, the proton attached to the hemiacetal hydroxyl group appears as a doublet at δ 7.12–8.02 with a coupling constant of 4.9–6.8 Hz. The proton at C-6 appears as a doublet at δ 4.97–5.61 with a coupling constant of 3.8–6.5 Hz. The cis-configuration of the protons at positions 5 and 11b and trans-configuration at positions 5 and 5a was assigned based on the coupling constants (J5a,11b=4 Hz, J5,5a=9 Hz). Additionally, the structure of 2i was obtained by single crystal X-ray crystallographic analysis (Figure 1).

Figure 1 ORTEP view of 2i showing displacement ellipsoids at the 30% probability level. Hydrogen atoms are shown as spheres of an arbitrary radius.
Figure 1

ORTEP view of 2i showing displacement ellipsoids at the 30% probability level. Hydrogen atoms are shown as spheres of an arbitrary radius.

The X-ray diffraction study of 2i showed that dihydrothiopyran and dihydropyran rings are fused in a cis-decalin mode. Moreover, the H atom pairs at the stereogenic centers C7 and C8 as well as at C7 and C16 centers are in cis configuration while protons at C6 and C7 centers are trans to each other. The torsion angles H7–C7–C8–H8, H7–C7–C16–H16 and H6-C6-C7-H7 amount to 60, 52 and 170°, respectively.

Conclusion

In summary, it was established that 5-arylideneisorhodanines with an ortho-phenolic group at arylidene moiety undergo a diastereoselective tandem hetero-Diels-Alder-hemiacetal reaction providing novel rel-(5aR,6R,11bS)-6-hydroxy-3,5a,6,11b-tetrahydro-2H,5H-chromeno[4′,3′:4,5]thiopyrano[2,3-d][1,3]thiazole-2-ones.

Experimental

All materials were purchased from commercial sources and used without purification. Melting points were measured in open capillary tubes and were uncorrected. The elemental analyses were performed using a Perkin–Elmer 2400 CHN analyzer. The 1H NMR (400 MHz) and 13C NMR (100 MHz) spectra were recorded on Varian Gemini 400 in DMSO-d6 using tetramethylsilane as an internal standard. Mass spectra were obtained using electrospray ionization (ESI) technique on an Agilent 1100 Series LC-MS instrument. The purity of all compounds was checked by TLC. The starting 4-thioxo-2-thiazolidinone was obtained according to method described previously [25]. 5-Arylidene-4-thioxo-2-thiazolidinones 1a–d were prepared by Knoevenagel condensation: a mixture of 4-thioxo-2-thiazolidinone (10 mmol), an aldehyde (10 mmol) and a catalytic amount of EDDA in ethanol 10 mL was heated under reflux for 10 min. The resultant solid product was filtered and used without further purification.

General procedure of hetero-Diels-Alder-hemiacetal reaction affording 2a–l

A mixture of a 5-(2-hydroxybenzylidene)-4-thioxo-2-thiazolidinone (10 mmol) and a dienophile (11 mmol) was heated under reflux for 1 h in 10 mL of glacial acetic acid. The mixture contained a catalytic amount of hydroquinone (2–3 mg) for preventing polymerization processes. After completion of the reaction, as determined by TLC analysis, the mixture was poured into water and the precipitated crystals were filtered off, washed with ethanol, and crystallized from solvent indicated below.

rel-(5aR,6R,11bS)-6-Hydroxy-3,5a,6,11b-tetrahydro-2H,5H-chromeno[4′,3′:4,5]thiopyrano[2,3-d][1,3]thiazole-2-one (2a)

Yield 70%; mp 168–170°C (EtOH); 1H NMR: δ 2.37 (m, 1H, 5-H), 2.87 (dd, 1H, J=8.2, 12.4 Hz, 5-H), 3.22 (m, 1H, 5a-H), 4.03 (d, 1H, J=5.0 Hz, 11b-H), 5.46 (t, 1H, J=4.6 Hz, 6-H), 6.75 (d, 1H, J=8.0 Hz, arom.), 6.88 (t, 1H, J=7.5 Hz, arom.), 7.13 (t, 1H, J=7.5 Hz, arom.), 7.24 (d, 1H, J=7.5 Hz, arom.), 7.53 (d, 1H, J=5.2 Hz, OH), 11.41 (s, 1H, NH); 13C NMR: δ 25.9, 31.6, 36.0, 92.9, 104.6, 117.3, 119.7, 121.2, 123.5, 128.9, 129.2, 151.2, 170.9; ESI-MS: m/z 294 (M+H)+. Anal. Calcd for C13H11NO3S2: C, 53.23; H, 3.78; N, 4.77. Found: C, 53.21; H, 3.77; N, 4.75.

rel-(5aR,6R,11bS)-6-Hydroxy-8-methoxy-3,5a,6,11b-tetrahydro-2H,5H-chromeno[4′,3′:4,5]thiopyrano[2,3-d][1,3]thiazole-2-one (2b)

Yield 76%; mp 202–204°C (EtOH); 1H NMR: δ 2.37 (m, 1H, 5-H), 2.67 (m, 1H, 5-H), 3.02 (m, 1H, 5-H), 3.78 (s, 3H, CH3O), 4.00 (d, 1H, J=4.2 Hz, 11b-H), 5.48 (t, 1H, J=5.1 Hz, 6-H), 6.78–6.88 (m, 3H, arom.) 7.46 (d, 1H, J=5.2 Hz, OH), 11.21 (s, 1H, NH); 13C NMR: δ 26.1, 31.9, 35.8, 55.9, 92.9, 104.9, 111.2, 119.6, 120.7, 123.8, 140.8, 148.7, 171.0; ESI-MS: m/z 324 (M+H)+. Anal. Calcd for C14H13NO4S2: C, 52.00; H, 4.05; N, 4.33. Found: C, 52.02; H, 4.07; N, 4.35.

rel-(5aR,6R,11bS)-10-Chloro-6-hydroxy-3,5a,6,11b-tetrahydro-2H,5H-chromeno[4′,3′:4,5]thiopyrano[2,3-d][1,3]thiazole-2-one (2c)

Yield 74%; mp 102–104°C (EtOH); 1H NMR: δ 2.90 (m, 1H, 5-H), 3.26 (m, 1H, 5-H), 3.31 (m, 1H, 5a-H) 4.09 (d, 1H, J=4.8 Hz, 11b-H), 5.49 (t, 1H, J=5.1 Hz, 6-H), 6.84 (d, 1H, J=8.4 Hz, arom.), 7.20 (d, 1H, J=9.2 Hz, arom.), 7.30 (s, 1H, arom.), 7.67 (d, 1H, J=5.2 Hz, OH), 11.51 (s, 1H, NH); 13C NMR: δ 25.7, 31.1, 35.7, 93.2, 103.5, 119.3, 120.3, 124.6, 125.6, 128.8, 129.4, 150.1, 170.9; ESI-MS: m/z 328/330 (M+H)+. Anal. Calcd for C13H10ClNO3S2: C, 47.63; H, 3.07; N, 4.27. Found: C, 47.62; H, 3.09; N, 4.25.

rel-(5aR,6R,11bS)-10-Bromo-6-hydroxy-3,5a,6,11b-tetrahydro-2H,5H-chromeno[4′,3′:4,5]thiopyrano[2,3-d][1,3]thiazole-2-one (2d)

Yield 75%; mp 131–133°C (EtOH); 1H NMR: δ 2.37 (m, 1H, 5-H), 2.91 (dd, 1H, J=8,9, 12.9 Hz, 5-H), 3.26 (m, 1H, 5a-H), 4.10 (d, 1H, J=4.8 Hz, 11b-H), 5.48 (t, 1H, J=4.9 Hz, 6-H), 6.78 (d, 1H, J=8.6 Hz, arom.), 7.34 (d, 1H, J=8.6 Hz, arom.), 7.42 (s, 1H, arom.), 7.67 (d, 1H, J=5.2 Hz, OH), 11.50 (s, 1H, NH); 13C NMR: δ 31.0, 33.4, 35.7, 93.2, 103.5, 112.3, 119.8, 126.7, 129.4, 131.6, 150.5, 170.9; ESI-MS: m/z 372/374 (M+H)+. Anal. Calcd for C13H10BrNO3S2: C, 41.94; H, 2.71; N, 3.76. Found: C, 41.92; H, 2.73; N, 3.75.

rel-(5S,5aR,6R,11bS)-6-Hydroxy-5-methyl-3,5a,6,11b-tetrahydro-2H,5H-chromeno[4′,3′:4,5]thiopyrano[2,3-d][1,3]thiazole-2-one (2e)

Yield 75%; mp 191–193°C (PhMe); 1H NMR: δ 1.55 (d, 3H, J=7.1 Hz, CH3), 2.13 (m, 1H, 5a-H), 3.55 (m, 1H, 5-H), 4.95 (d, 1H, J=6.0 Hz, 11b-H), 5.33 (t, 1H, J=6.0 Hz, 6-H), 6.74 (d, 1H, J=7.8 Hz, arom.), 6.86 (t, 1H, J=7.1 Hz, arom.), 7.06–7.13 (m, 2H, arom.), 7.33 (d, 1H, J=5.1 Hz, OH), 11.10 (s, 1H, NH); 13C NMR: δ 21.0, 30.7, 35.4, 41.2, 93.0, 104.7, 117.0, 118.5, 120.9, 125.3, 129.0, 130.1, 152.3, 171.0; ESI-MS: m/z 308 (M+H)+. Anal. Calcd for C14H13NO3S2: C, 54.70; H, 4.26; N, 4.56. Found: C, 54.71; H, 4.24; N, 4.57.

rel-(5S,5aR,6R,11bS)-6-Hydroxy-8-methoxy-5-methyl-3,5a,6,11b-tetrahydro-2H,5H-chromeno[4′,3′:4,5]thiopyrano[2,3-d][1,3]thiazole-2-one (2f)

Yield 70%; mp 202–204°C (PhMe); 1H NMR: δ 1.49 (d, 3H, J=6.5 Hz, CH3), 2.13 (dd, 1H, J=4.9, 11.6 Hz, 5a-H), 3.54 (m, 1H, 5-H), 3.77 (s, 3H, CH3O), 3.93 (d, 1H, J=4.2 Hz, 11b-H), 5.33 (t, 1H, J=6.2 Hz, 6-H), 6.80 (t, 1H, J=7.2 Hz, arom.), 7.12 (d, 1H, J=7.2 Hz, OH), 7.19 (d, 1H, J=7.2 Hz, arom.), 7.50 (t, 1H, J=7.2 Hz, arom.), 11.13 (s, 1H, NH); 13C NMR: δ 21.1, 30.7, 35.4, 41.0, 55.9, 93.2, 104.8, 111.4, 118.4, 120.5, 123.4, 129.4, 141.8, 148.5, 171.0; ESI-MS: m/z 338 (M+H)+. Anal. Calcd for C15H15NO4S2: C, 53.40; H, 4.48; N, 4.15. Found: C, 53.41; H, 4.47; N, 4.16.

rel-(5S,5aR,6R,11bS)-10-Chloro-6-hydroxy-5-methyl-3,5a,6,11b-tetrahydro-2H,5H-chromeno[4′,3′:4,5]thiopyrano[2,3-d][1,3]thiazole-2-one (2g)

Yield 77%; mp 142–144°C (PhMe); 1H NMR: δ 1.14 (d, 3H, J=6.9 Hz, CH3), 2.20 (dd, 1H, J=5.4, 12.0 Hz, 5a-H), 2.30 (m, 1H, 5-H), 4.08 (d, 1H, J=4.8 Hz, 11b-H), 5.32 (t, 1H, J=6.3 Hz, 6-H), 6.85 (d, 1H, J=8.7 Hz, arom.), 7.22–7.31 (m, 2H, arom.), 7.71 (d, 1H, J=6.0 Hz, OH), 11.40 (s, 1H, NH); 13C NMR: δ 20.8, 30.5, 35.4, 93.2, 103.8, 118.9, 119.1, 124.4, 125.1, 128.7, 129.0, 129.4, 151.2, 170.9; ESI-MS: m/z 342 (M+H)+. Anal. Calcd for C14H12ClNO3S2: C, 49.19; H, 3.54; N, 4.10. Found: C, 49.22; H, 3.55; N, 4.12.

rel-(5S,5aR,6R,11bS)-10-Bromo-6-hydroxy-5-methyl-3,5a,6,11b-tetrahydro-2H,5H-chromeno[4′,3′:4,5]thiopyrano[2,3-d][1,3]thiazole-2-one (2h)

Yield 72%; mp 182–184°C (PhMe); 1H NMR: δ 1.43 (d, 3H, J=6.9 Hz, CH3), 2.19 (dd, 1H, J=5.1,11.6 Hz, 5a-H), 3.52 (m, 1H, 5-H), 4.08 (d, 1H, J=5.0 Hz, 11b-H), 5.31 (t, 1H, J=6.0 Hz, 6-H), 6.79 (d, 1H, J=8.7 Hz, arom.), 7.33 (d, 1H, J=8.5 Hz, arom.), 7.42 (s, 1H, arom.), 7.70 (d, 1H, J=6.3 Hz, OH), 11.40 (s, 1H, NH); 13C NMR: δ 20.7, 30.6, 35.4, 93.2, 103.8, 111.9, 125.7, 125.8, 128.7, 129.4, 131.9, 151.7, 170.9. ESI-MS m/z 386/388 (M+H)+. Anal. Calcd for C14H12BrNO3S2: C, 43.53; H, 3.13; N, 3.63. Found: C, 43.54; H, 3.14; N, 3.65.

rel-(5S,5aR,6R,11bS)-6-hydroxy-5-phenyl-3,5a,6,11b-tetrahydro-2H,5H-chromeno[4′,3′:4,5]thiopyrano[2,3-d][1,3]thiazole-2-one (2i)

Yield 71%; mp 188–190°C (PhMe); 1H NMR (400 MHz, DMSO-d6): δ 2.59 (dd, 1H, J=4.3, 8.7 Hz, 5a-H), 3.98 (d, 1H, J=3.6 Hz, 11b-H), 4.38 (d, 1H, J=8.8 Hz, 5-H), 5.01 (t, 1H, J=3.9 Hz, 6-H), 6.76 (d, 1H, J=8.1 Hz, arom.), 6.66 (t, 1H, J=7.4 Hz, arom.), 7.08–7.14 (m, 2H, arom.), 7.49 (d, 1H, J=4.9 Hz, OH), 11.32 (s, 1H, NH); 13C NMR: δ 30.3, 41.6, 44.0, 91.4, 103.6, 117.4, 120.3, 121.4, 123.4, 125.8, 128.7, 128.8, 128.9, 129.4, 138.3, 150.1, 171.1; ESI-MS: m/z 370 (M+H)+. Anal. Calcd for C19H15NO3S2: C, 61.77; H, 4.09; N, 3.79. Found: C, 61.75; H, 4.07; N, 3.80.

rel-(5S,5aR,6R,11bS)-6-Hydroxy-8-methoxy-5-phenyl-3,5a,6,11b-tetrahydro-2H,5H-chromeno[4′,3′:4,5]thiopyrano[2,3-d][1,3]thiazole-2-one (2j)

Yield 90%; mp 170–172°C (PhMe); 1H NMR: δ 2.33 (m, 1H, 5a-H), 3.77 (s, 3H, CH3O), 3.90 (m, 1H, 11b-H), 4.41 (d, 1H, J=9.2 Hz, 5-H), 5.08 (t, 1H, J=3.9 Hz, 6-H), 6.80–6.87 (m, 3H, arom.), 7.34–7.40 (m, 6H, arom., OH), 11.35 (s, 1H, NH); 13C NMR: δ 30.5, 41.5, 43.9, 56.0, 91.5, 103.9, 111.5, 120.2, 120.4, 120.9, 123.7, 128.7, 128.8, 129.4, 138.6, 140.6, 148.7, 171.2; ESI-MS: m/z 400 (M+H)+. Anal. Calcd for C20H17NO4S2: C, 60.13; H, 3.29; N, 3.51. Found: C, 60.12; H, 3.28; N, 3.53.

rel-(5S,5aR,6R,11bS)-10-Chloro-6-hydroxy-5-phenyl-3,5a,6,11b-tetrahydro-2H,5H-chromeno[4′,3′:4,5]thiopyrano[2,3-d][1,3]thiazole-2-one (2k)

Yield 78%, mp 190–192°C (PhMe); 1H NMR: δ 2.75 (dd, 1H, J=4.8, 9.6 Hz, 5a-H), 4.10 (d, 1H, J=4.8 Hz, 11b-H), 4.36 (d, 1H, J=9.4 Hz, 5-H), 4.98 (t, 1H, J=4.6 Hz, 6-H), 6.87 (d, 1H, J=8.7 Hz, arom.), 7.12–7.20 (m, 2H, arom.), 7.65 (d, 1H, J=4.6 Hz, OH), 11.44 (s, 1H, NH); 13C NMR: δ 30.2, 41.0, 43.9, 91.4, 102.6, 119.4, 121.0, 124.9, 125.8, 128.4, 128.6, 128.7, 128.9, 129.4, 137.8, 149.8, 171.1; ESI-MS: m/z 404/406 (M+H)+. Anal. Calcd for C19H14ClNO3S2: C, 56.50; H, 3.49; N, 3.47. Found: C, 56.52; H, 3.51; N, 3.46.

rel-(5S,5aR,6R,11bS)-10-Bromo-6-hydroxy-5-phenyl-3,5a,6,11b-tetrahydro-2H,5H-chromeno[4′,3′:4,5]thiopyrano[2,3-d][1,3]thiazole-2-one (2l)

Yield 75%, mp 217–219°C (PhMe); 1H NMR: δ 2.62 (dd, 1H, J=5.6, 10.9 Hz, 5a-H), 4.03 (m, 1H, 11b-H), 4.31 (d, 1H, J=9.5 Hz, 5-H), 4.97 (m, 1H, 6-H), 6.74 (d, 1H, J=8.4 Hz, arom.), 7.26 (d, 1H, J=7.6 Hz, arom.), 7.31–7.51 (m, 2H, OH, arom.), 11.44 (s, 1H, NH); 13C NMR: δ 30.1, 41.0, 43.9, 91.4, 102.5, 112.6, 119.9, 121.0, 126.2, 128.9, 129.4, 131.3, 131.6, 17.8, 150.3, 171.1; ESI-MS: m/z 448/450 (M+H)+. Anal. Calcd for C19H14BrNO3S2: C, 50.90; H, 3.15; N, 3.12. Found: C, 50.91; H, 3.13; N, 3.14.

X-ray crystallographic study

Crystallographic data for 2i: Empirical formula C19H15NO3S2·H2O, formula weight 387.45, light-brown block crystals, crystal system monoclinic, space group P21/c, a=10.9127(4), b=15.1717(4), c=11.2980(4) Å, β=111.457(4)°, V=1740.90(11) Å3, Z=4, Dcalc=1.478 g/cm3. A light-brown crystal (benzene-acetone) (0.17×0.13×0.07 mm) was used to record 17 948 (CuKα-radiation, θmax=76.38°) intensities on a Super Nova diffractometer. The supplementary crystallographic data of 2i have been deposited at the Cambridge Crystallography Data Centre (CCDC) as supplementary publication CCDC 1497433. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK, (fax: +44-(0)1223-336033 or e-mail: deposit@ccdc.cam.ac.uk).

Acknowledgments

This work was partially supported by the Ministry of Education and Science of Ukraine (Ukrainian-France program ‘Dnipro’ M/188-2015; 06.11.2015).

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Received: 2016-10-15
Accepted: 2016-11-9
Published Online: 2017-1-28
Published in Print: 2017-2-1

©2017 Walter de Gruyter GmbH, Berlin/Boston

This article is distributed under the terms of the Creative Commons Attribution Non-Commercial License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.

Articles in the same Issue

  1. Frontmatter
  2. Preliminary Communications
  3. Tandem hetero-Diels–Alder-hemiacetal reaction in the synthesis of new chromeno[4′,3′:4,5]thiopyrano[2,3-d]thiazoles
  4. A new method for the reaction of cross-coupling: preparation of 5,5′-bi(1,10-phenanthroline)
  5. Design and synthesis of 4,5-diaryl/heteroarylthiophene-2-carboxylic acid derivatives and evaluation of their biological activities
  6. Research Articles
  7. Synthesis and properties of dicarbazolyltriphenylethylene-substituted fluorene derivatives exhibiting aggregation-induced emission enhancement
  8. Synthesis of a new polycyclic heterocyclic ring system. Part III. Benzo[b]imidazo[1,5-d][1,4]oxazepine-1,4(2H,5H)-diones
  9. Br2- or HBr-catalyzed synthesis of asymmetric 3,3-di(indolyl)indolin-2-ones
  10. Mono- and bis-dipicolinic acid heterocyclic derivatives – thiosemicarbazides, triazoles, oxadiazoles and thiazolidinones as antifungal and antioxidant agents
  11. Synthesis and antimicrobial activity of new piperazine-based heterocyclic compounds
  12. Synthesis and evaluation of chromene-based compounds containing pyrazole moiety as antimicrobial agents
  13. Ultrasonic synthesis, characterization, and antibacterial evaluation of novel heterocycles containing hexahydroquinoline and pyrrole moieties
https://doi.org/10.1515/hc-2016-0176
Keywords for this article
hetero-Diels-Alder-hemiacetal reaction; tandem reactions; thiopyrano[2,3-d][1,3]thiazoles; 4-thioxo-2-thiazolidinones; X-ray analysis
Creative Commons
BY-NC-ND 3.0

Articles in the same Issue

  1. Frontmatter
  2. Preliminary Communications
  3. Tandem hetero-Diels–Alder-hemiacetal reaction in the synthesis of new chromeno[4′,3′:4,5]thiopyrano[2,3-d]thiazoles
  4. A new method for the reaction of cross-coupling: preparation of 5,5′-bi(1,10-phenanthroline)
  5. Design and synthesis of 4,5-diaryl/heteroarylthiophene-2-carboxylic acid derivatives and evaluation of their biological activities
  6. Research Articles
  7. Synthesis and properties of dicarbazolyltriphenylethylene-substituted fluorene derivatives exhibiting aggregation-induced emission enhancement
  8. Synthesis of a new polycyclic heterocyclic ring system. Part III. Benzo[b]imidazo[1,5-d][1,4]oxazepine-1,4(2H,5H)-diones
  9. Br2- or HBr-catalyzed synthesis of asymmetric 3,3-di(indolyl)indolin-2-ones
  10. Mono- and bis-dipicolinic acid heterocyclic derivatives – thiosemicarbazides, triazoles, oxadiazoles and thiazolidinones as antifungal and antioxidant agents
  11. Synthesis and antimicrobial activity of new piperazine-based heterocyclic compounds
  12. Synthesis and evaluation of chromene-based compounds containing pyrazole moiety as antimicrobial agents
  13. Ultrasonic synthesis, characterization, and antibacterial evaluation of novel heterocycles containing hexahydroquinoline and pyrrole moieties
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