Iodine-Mediated Cyclization Unveils a Serene Path to 2-Thioxo-2,3- Dihydroquinazolin-4(1H)-one Derivatives through the Harmonious Union of 2-Aminobenzyl Alcohol and Isothiocyanates

doi:10.21203/rs.3.rs-3562074/v1

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Iodine-Mediated Cyclization Unveils a Serene Path to 2-Thioxo-2,3- Dihydroquinazolin-4(1H)-one Derivatives through the Harmonious Union of 2-Aminobenzyl Alcohol and Isothiocyanates

https://doi.org/10.21203/rs.3.rs-3562074/v1

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In this paper, a novel and facile method is reported for the synthesis of 2-thioxoquinazolinone. For the synthesis of the products, a reaction is introduced based on the molecular iodine catalyzed reaction of 2-aminobenzyl alcohol and isothiocyanates in DMSO. The reaction is simple and the products are obtained in good to excellent yields. FT-IR, ¹H NMR and ¹³C NMR spectra were used for the exact characterization of all the products.

2-thioxoquinazolinone

2-aminobenzyl alcohol

isothiocyanates

molecular iodine catalyst

Benzoquinazoline and its derivatives are significant, due to their wide range of pharmacological and biological activities[1], including antitumor[2], antifungal[3], analgesic[4], antimalarial[5], phosphodiesterase inhibitor[6], anti-inflammatory[7], anticonvulsant[8] and antimicrobial[9, 10] properties. In addition, 2-thioxoquinazolinone derivatives with quinazoline framework have wide biological activities[11]. Furthermore, 2-thioxoquinazolinone structure is widely used in the synthesis of many commercial drugs such as ¹⁸F-altanserin for serotonin receptor [12] (Fig. 1).

Regarding the significance of 2-thioxoquinazolinones, several efforts have been focused on the synthesis of this class of organic compounds [13–16]. However, most of the reported methods suffer a number of disadvantages, including low isolated yields of the products, harsh reaction conditions, and the use of hazardous solvents [17]. Therefore, this is a challenge among researchers to introduce the synthetic methods, which are efficient and facile via environmentally friendly processes.

Several methods have been reported for the synthesis of 2-thioxoquinazolinones. A common substrate class for the synthesis of these compounds, are benzoic acid derivatives with a nitrogen functionality in ortho position. amine, isocyanate, and amides are a number of substrates, which are used for the synthesis of 2-thioxoquinazolinones. In other reports, 2-thioxoquinazolinone derivatives were synthesized by phenyl isothiocyanates and 2-aminobenzoic acids in various solvents such as ethanol, toluene and acetic acid in the absence of catalysts [18–23].

Regarding the significance of 2-thioxoquinazolinone derivatives, and following our ongoing projects on the synthesis of organic compounds via facile and efficient methods, we hereby reported a simple method for the synthesis of 2-thioxoquinazolinone derivatives (3a-n). The method is based on the reaction of 2-aminobenzyl alcohol (1) with isothiocyanates (2a-n) in DMSO in the present of I₂ as catalyst at 100°C. the reaction is presented in Fig. 2.

In this paper, a novel and efficient method is reported for the synthesis of 2-thioxoquinazolinone derivatives. The synthesis is based on the reaction of (2-aminophenyl)methanol and isothiocyanatobenzene in the presence of a catalyst. For the synthesis of the desired products in the most efficient way, the reaction conditions were optimized. Based on the optimized reaction conditions, the scope and generality of the method was evaluated by using various substrates. The structure of the synthesized products were confirmed by FT-IR, ¹H NMR, ¹³C NMR and mass spectroscopy. To optimize the reaction conditions, the reaction between 2-aminobenzyl alcohol and phenyl isothiocyanate was selected as the model reaction. The optimization reactions were performed in the presence diverse amounts of molecular I₂ and different solvents for the synthesis of phenyl-2‐thioxo‐2,3‐dihydroquinazolin‐4(1H)‐one (3a). In addition, to choose the best temperature, the selected model reaction was studied at different temperatures in the presence of I₂ (0.4 eq.) in DMSO for 3h (Table 1, entries 1–4). Then, the amount of I₂ catalyst was investigated (Table 1, entries 4–6). For this purpose, the reaction was performed in the presence of various amounts of the catalyst (0.2, 0.4 and 0.6 eq.) and the yields of the products were compared. To improve the model reaction yields, the reaction was performed in different solvents such as toluene, H₂O and DMF and solvent free condition (Table 1, entries 7–11). Based on the optimization results, the optimal reaction conditions were selected as DMSO solvent at 100°C in the presence of o.4 eq. of I₂ catalyst (Table 1, entry 4).

Using the optimum conditions for the synthesis of phenyl-2‐thioxo‐2,3‐dihydroquinazolin‐4(1H) ‐one (3a), various product derivatives were synthesized using a wide range of substrates (Table 2).

The proposed mechanism for the synthesis of phenyl-2‐thioxo‐2,3‐dihydroquinazolin‐4(1H)‐one is shown in scheme 2. In the first step, 2-aminobenzyl alcohol (1) is converted to (2-aminophenyl) hypoiodite (2) in the presence of I₂, which converts to 2-aminobenzaldehyde (3) by the removal of an HI molecule [27]. Then, 2-aminobenzaldehyde is subjected to nucleophilic addition reaction with phenyl isothiocyanate (4), which results in the synthesis of intermediate (5). Intermediate (5) undergoes an intermolecular nucleophilic addition reaction in the presence of I₂ that results in the synthesis of intermediate (6). Finally, the desired product is formed by removal of HI. I₂ can be re-prepared by oxidizing HI with DMSO in two steps.

To demonstrate the superiority of this method over the methods performed, we compared the yield of the reaction of 2-aminobenzyl alcohol and phenyl isothiocyanate under the optimized reaction conditions in this paper with previous works (Table 3). This method provides excellent yields (up to 95%) in propriety time.

Table 3

Efficiency comparison of I₂, DMSO with the reported catalysts for synthesis of phenyl-2‐thioxo‐2,3‐dihydroquinazolin‐4(1H)‐one
Entry	Catalyst	Solvent	Yield (%)	Ref.
1	choline chloride	eutectic solvent	90	[18]
2	KSCN	H₂O	85	[24]
3	NiFe₂O₄@SiO₂–PPA ^[a]	solvent-free	91	[28]
4	I2	DMSO	95	This work

[a] PPA = Polyphosphoric acid.

In this paper, we present a novel method for the synthesis of 2-thioxo-2,3-dihydroquinazolin-4(1H)-one derivatives. This method involves a nucleophilic addition reaction of 2-aminobenzyl alcohol with isothiocyanate derivatives in DMSO solvent at 100°C in the presence of I₂ as the catalyst. The most important advantages of this reaction include the facile reaction conditions, commercially availability of the substrates, and excellent products yields.

General remarks

All the chemicals, Solvents and reagents were purchased from Merck, Germany, and Sigma, USA and used as received.1H and ¹³C NMR spectra were obtained on a Bruker Avance 500 NMR spectrometer in DMSO-d₆ and CDCl₃ as solvents. Mass spectra were recorded on an Agilent Technology (HP) mass spectrometer with an ionization potential of 70 eV.

General procedure for the synthesis of 2-thioxoquinazolinone derivatives

A mixture of 2-aminobenzyl alcohol (123 mg, 1 mmol) and isothiocyanates derivatives (1 mmol) were dissolved in DMSO (3 mL) and stirred for 2–3 h at 100°C in the presence of I₂ (0.4 eq.). The reaction performance was monitored by TLC. After completion of the reaction, the product was obtained as a precipitate, which was filtered, washed well with H₂O and recrystallized from hot water and ethanol to gain the pure white product.

Spectral data of the products

3-Phenyl‐2‐thioxo‐2,3‐dihydroquinazolin‐4(1H)‐one (3a)

White solid; m. p.232–234°C; IR (KBr, ν, cm^-1): 3246, 3033, 1666, 1623, 1531, 1489.¹H NMR (500 MHz, DMSO-d₆):δ = 7.22–7.24 (m, 2H, H Ar), 7.34 (t, J = 7.5 Hz, 1H, H Ar), 7.41–7.49 (m, 4H, H Ar), 7.76 (td, J = 7.5, 1.1 Hz, 1H, H Ar), 7.95 (dd, J = 8.0Hz, 1H, H Ar), 13.01 (s, 1H, NH). ¹³C NMR (125 MHz, DMSO‐d₆):δ = 115.2, 116.3, 124.1, 127.4, 128.3, 128.8, 129.1, 135.3, 139.3, 139.6, 159.7, 175.2. MS (70 eV): m/z = 254.06 (M⁺).

3-(2‐Chlorobenzyl)‐2‐thioxo‐2,3‐dihydroquinazolin‐4(1 H )‐one (3b)

White solid; m. p.230–232°C; IR (KBr, ν, cm^-1): = 3180, 3031, 1695, 1, 622, 1542, 1485.¹H NMR (500 MHz, DMSO-d₆):δ = 5.86 (s, 2H, N-CH₂), 6.95 (d, J = 7.5 Hz, H Ar), 7.11–7.15 (m, 2H, H Ar), 7.18 (t, J = 7.7 Hz, H Ar), 7.32 (t, J = 7.5 Hz, H Ar), 7.41 (d, J = 7.5 Hz, H Ar), 7.71 (t, J = 7.5 Hz, H Ar), 8.17 (d, J = 7.5 Hz, H Ar), 10.11 (s, 1H, NH). ¹³C NMR (125 MHz, DMSO‐d₆):δ = 46.0, 114.1, 125.3, 125.8, 126.6, 128.1, 128.8, 129.6, 131.2, 132.8, 135.1, 135.6, 138.2, 159.6, 176.3. m/z = 302.04 (M⁺).

3-(4‐Chlorobenzyl)‐2‐thioxo‐2,3‐dihydroquinazolin‐4(1 H )‐one (3c)

White solid, m. p.226–228°C; IR (KBr, ν, cm-1): 3251, 3069, 1662, 1621, 1592, 1530, 1481.¹H NMR (500MHz, DMSO-d₆):δ = 5.74 (s, 2H, N-CH₂), 6.91 (d, J = 7.0 Hz, 2H, H Ar), 7.29–7.33 (m,3H, H Ar), 7.44 (d, J = 7.5 Hz, H Ar), 7.72 (t, J = 7.5 Hz, H Ar), 7.91 (d, J = 7.5 Hz, H Ar), 12.98 (s, 1H, NH). ¹³C NMR (125 MHz, DMSO‐d₆):δ = 54.3, 112.8, 115.1, 115.5, 124.0, 126.7, 127.6, 128.4, 134.4, 139.0, 158.6, 158.8, 175.1.

3-(4‐Methoxybenzyl)‐2‐thioxo‐2,3‐dihydroquinazolin‐4(1 H )‐one (3d)

White solid; m. p.231–233°C; IR (KBr, ν, cm-1): 3252, 3071, 1663, 1623, 1592, 1533, 1481.¹H NMR (500MHz, DMSO-d₆):δ = 3.70 (s,3H, OCH₃), 5.78 (s, 2H, N-CH₂), 6.86 (d, J = 6.5 Hz, 2H, H Ar), 7.31–7.34 (m,3H, H Ar), 7.45 (d, J = 8.0 Hz, H Ar), 7.75 (t, J = 8.0 Hz, H Ar), 7.95 (d, J = 8.0 Hz, H Ar), 13.03 (s, 1H, NH). ¹³C NMR (125 MHz, DMSO‐d₆):δ = 48.1, 55.1, 113.3, 115.4, 115.5, 124.5, 127.2, 128.5, 129.1, 135.5, 139.2, 158.5, 159.2, 175.5.

3-(2-methoxyphenethyl)‐2‐thioxo‐2,3‐dihydroquinazolin‐4(1 H )‐one (3e)

White solid; m. p.202–204°C; IR (KBr, ν, cm^-1): = 3263, 3081, 1665, 1626, 1595, 1531, 1480.¹H NMR (500MHz, DMSO-d₆):δ = 2.96 (t, J = 7.6 Hz, 2H, NCH₂CH₂),3.72 (s,3H, OCH₃), 4.62 (t, J = 7.6 Hz, H Ar), 6.85 (t, J = 7.5 Hz, H Ar), 6.92 (d, J = 7.5 Hz, 1H, H Ar), 7.15–7.20 (m, 2H, H Ar), 7.32 (m, J = 7.6, 1.1 Hz, H Ar), 7.36 (d, J = 7.6 Hz, H Ar), 7.76 (m, J = 7.6, 1.1 Hz, H Ar), 7.94 (dd, J = 7.6, 1.1 Hz, H Ar), 12.91 (s, 1H, NH). ¹³C NMR (125.8 MHz, DMSO‐d₆):δ = 26.6, 45.2, 55.1, 110.5, 115.3, 120.2, 124.2, 126.3, 127.1, 127.6, 129.6, 135.2, 136.1, 139.1, 157.2, 159.2, 175.1. MS (70 eV):m/z = 312.06(M⁺).

3-(3,4-dimethoxyphenethyl)‐2‐thioxo‐2,3‐dihydroquinazolin‐4(1 H )‐one (3f)

White solid; m. p.231–233°C; IR (KBr, ν, cm^-1): 3181, 3041, 1685, 1621, 1588, 1540, 1480. ¹H NMR(500 MHz, DMSO-d₆):δ = 2.90 (t, J = 8.0 Hz, 2H, NCH₂),3.71(s,3H, OCH₃),3.72 (s,3H, OCH₃), 4.56 (t, J = 8.0 Hz, 2H, Ar-CH₂), 6.80 (d, J = 8.5 Hz, 1H, H Ar), 6.85–6.88(m, 2H, H Ar), 7.32 (t, J = 8.0 Hz, H Ar), 7.41 (d, J = 8.0 Hz, H Ar), 7.73 (t, J = 8.0 Hz, H Ar), 7.95 (d, J = 8.0 Hz, H Ar), 12.95 (s, 1H, NH). ¹³C NMR(125 MHz, DMSO‐d₆): 31.6, 47.0, 55.2, 55.4, 112.1, 112.2, 115.4, 115.5, 120.4, 124.6, 127.1, 130.8, 135.5, 139.1, 147.6, 148.6, 159.0, 174.8. MS (70 eV): m/z = 342.09 (M⁺)

3-(3,4-dimethoxyphenyl)‐2‐ thioxo‐2,3‐dihydroquinazolin‐4(1 H )‐one (3g)

White solid; m. p.246–248°C; IR (KBr, ν, cm^-1): 3181,3032, 1697, 1646, 1621, 1536, 1485. ¹H NMR (500 MHz, DMSO-d₆):δ = 3.70 (s,3H, OCH₃),3.80 (s,3H, OCH₃), 6.81 (dd, J = 8.5, 2.5 Hz, Ar-H), 6.91 (d, J = 2.2 Hz, Ar-H), 7.01 (d, J = 8.4 Hz, Ar-H), 7.35 (t, J = 7.6 Hz, Ar-H), 7.45 (d, J = 7.6 Hz, Ar-H), 7.76 (M, J = 7.6, Ar-H), 7.96 (dd, J = 7.6, Ar-H), 13.05 (s, 1H, NH). ¹³C NMR (125.8 MHz, DMSO‐d₆):δ = 55.4, 55.5, 111.5, 112.6, 115.5, 116.2, 121.1, 124.3, 127.5, 132.1, 135.6, 139.6, 148.5, 148.8, 159.6, 176.5. MS (70 eV): m/z = 314.05(M⁺).

3-Benzyl‐2‐thioxo‐2,3‐dihydroquinazolin‐4(1H)‐one (3h)

White solid; m. p.247–249°C; IR (KBr, ν, cm^-1): 3176,3028, 1695, 1646, 1622, 1532, 1485. ¹HNMR (500 MHz, DMSO-d₆):δ = 5.25 (s, 2H, NCH₂), 7.18–7.26 (m, 7H, H Ar), 7.75–782 (m, 2H, H Ar), 12.03 (b, 1H, NH). ¹³CNMR (125 MHz, DMSO‐d₆):δ = 50.3, 116.2, 116.5, 124.8, 126.2, 127.6, 129.2, 140.6, 127.8, 135.6, 140.5, 159.6, 175.1. MS (70 eV): m/z = 268.08 (M⁺).

3-(Pyridin‐2‐ylmethyl)‐2‐thioxo‐2,3‐dihydroquinazolin‐4(1H)‐one (3i)

White solid; m. p.262–264°C; IR (KBr, ν, cm^-1): 3266, 3070, 1666, 1625, 1592, 1530, 1482. ¹HNMR (500 MHz, DMSO-d₆):δ = 5.75 (s, 2H, NCH₂), 7.20 (t, J = 7.5 Hz, 1H, H Ar), 7.25 (d, J = 7.5 Hz, 1H, H Ar), 7.35 (t, J = 7.5 Hz, 1H, H Ar), 7.42 (d, J = 7.2 Hz, 1H, H Ar), 7.70 (t, J = 7.2 Hz, 1H, H Ar), 7.78 (t, J = 7.5 Hz, 1H, H Ar), 7.95 (d, J = 7.5 Hz, 1H, H Ar), 8.40 (t, J = 7.2 Hz, 1H, H Ar), 13.02 (s, 1H, NH). ¹³C NMR (125 MHz, DMSO‐d₆, δ, ppm):δ = 50.1, 115.2, 115.5, 120.5, 121.7, 124.3, 127.2, 135.4, 136.3, 139.0, 148.6, 155.2, 159.2, 175.4. MS (70 eV): m/z (%) = 269.07 (M⁺)

3-2,3‐Dihydro‐3‐isopropyl‐2‐thioxoquinazolin‐4(1H)‐one (3j)

White solid; m. p.204–206°C; IR (KBr, ν, cm-1): 3186, 3052, 1690, 1626, 1623, 1533, 1480. ¹HNMR (500 MHz, DMSO-d₆):δ = 1.01 (d, J = 7.0 Hz, 6H, CH₃), 6.02 (q, J = 7.0 Hz, 1H, CH), 7.30 (t, J = 8.0 Hz, 1H, H Ar), 7.32 (d, J = 8.0 Hz, 1H, H Ar), 7.65 (td, J = 8.0, 1H, H Ar), 8.13 (dd, J = 8.0, 1.2 Hz, 1H, H Ar), 12.85 (s, 1H, NH, NH). ¹³C NMR (125 MHz, DMSO‐d₆):δ = 18.3, 52.3, 115.1, 116.5, 124.2, 126.7, 135.0, 138.6, 159.2, 175.0. MS (70 eV): m/z = 220.08 (M⁺).

3-Propyl‐2‐thioxo‐2,3‐ dihydroquinazolin‐4(1H)‐one (3k)

White solid; m. p.170–172°C; IR (KBr, ν, cm^-1): 3192, 3050, 1697, 1642, 1624, 1533, 1480. ¹H NMR (500 MHz, DMSO-d₆):δ = 1.02 (t, J = 7.5 Hz,3H, CH₃), 1.84 (m, J = 7.5 Hz, 2H, CH₂), 4.52 (t, J = 7.5 Hz, 2H, CH₂), 7.21 (d, J = 7.5 Hz, 1H, H Ar), 7.30 (t, J = 7.5 Hz, 1H, H Ar), 7.63 (t, J = 7.7, 1.3 Hz, 1H, H Ar), 8.13 (dd, J = 7.5, 1.3 Hz, 1H, H Ar), 10.92 (s, 1H, NH). ¹³C NMR (125 MHz, DMSO‐d₆):δ = 11.1, 20.2, 48.2, 114.4, 116.1, 125.2, 128.4, 135.1, 138.2, 159.4, 175.5. MS (70 eV): m/z = 220.08 (M⁺).

3-[(Furan‐2‐yl)methyl]‐2,3‐dihydro‐2‐thioxoquinazolin‐4(1H)‐one (3l)

White solid; m. p.232–234°C; IR (KBr, ν, cm^-1): 3244, 3042, 1656, 1620, 1531, 1486. ¹H NMR(500 MHz, DMSO-d₆): 5.63 (s, 2H, NCH₂), 6.32(dd, J = 3.1, 1H, Furan), 6.35 (dd, J = 3.1, 1H, Furan), 7.32 (t, J = 7.5 Hz, 1H, H Ar), 7.37 (d, J = 7.5 Hz, 1H, H Ar), 7.51–7.50 (m, 1H, Furan), 7.71 (td, J = 7.5, 1.1 Hz, 1H, H Ar), 7.95 (dd, J = 7.5, 1.3 Hz, 1H, H Ar), 13.01 (s, 1H, NH). ¹³C NMR (125 MHz, DMSO‐d₆): 42.1, 108.1, 110.3, 115.1, 115.5, 124.4, 127.1, 135.5, 136.2, 139.2, 142.2, 159.2, 175.2. MS (70 eV): m/z(%) = 258.06 (M⁺).

Acknowledgements

We are appreciate of Payame Noor University for their support of this work.

Author Contributions Statement

MHS did the experiments, analysed the data, led the research, and corrected the manuscript; AS did the experiments and characterized the products; MY did the experiments and prepared the draft; FS did the experiments and prepared the draft; MM characterized the products; SB analysed the data, corrected the draft, and led the research.

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Tables 1-2 is available in the Supplementary Files section.

Scheme 2 is available in the Supplementary Files section.

No competing interests reported.

Table12.docx
Scheme2.png
Scheme 2. Proposed reaction mechanism of the reaction.

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Iodine-Mediated Cyclization Unveils a Serene Path to 2-Thioxo-2,3- Dihydroquinazolin-4(1H)-one Derivatives through the Harmonious Union of 2-Aminobenzyl Alcohol and Isothiocyanates

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General procedure for the synthesis of 2-thioxoquinazolinone derivatives

Spectral data of the products

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References

Tables

Scheme

Additional Declarations

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