A Domino Process for the Sustainable Synthesis of Quinazolin-4(3H)-ones with Direct Chemo- and Regioselective Bromination

Ehsan Sheikhi; Mehdi Adib; Rozita Yazzaf; Mehdi Jahani; Mehdi Ghavidel

doi:10.1055/s-0037-1610226

Synlett, Table of Contents

Synlett 2018; 29(15): 2046-2050
DOI: 10.1055/s-0037-1610226

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A Domino Process for the Sustainable Synthesis of Quinazolin-4(3H)-ones with Direct Chemo- and Regioselective Bromination

Ehsan Sheikhi *

^aSchool of Chemistry, College of Science, University of Tehran, PO Box 14155-6455, Tehran, Iran Email: ehsan.sheikhi@gmail.com Email: madib@khayam.ut.ac.ir

,

Mehdi Adib*

^aSchool of Chemistry, College of Science, University of Tehran, PO Box 14155-6455, Tehran, Iran Email: ehsan.sheikhi@gmail.com Email: madib@khayam.ut.ac.ir

,

Rozita Yazzaf

^aSchool of Chemistry, College of Science, University of Tehran, PO Box 14155-6455, Tehran, Iran Email: ehsan.sheikhi@gmail.com Email: madib@khayam.ut.ac.ir

,

Mehdi Jahani

^aSchool of Chemistry, College of Science, University of Tehran, PO Box 14155-6455, Tehran, Iran Email: ehsan.sheikhi@gmail.com Email: madib@khayam.ut.ac.ir

,

Mehdi Ghavidel

^aSchool of Chemistry, College of Science, University of Tehran, PO Box 14155-6455, Tehran, Iran Email: ehsan.sheikhi@gmail.com Email: madib@khayam.ut.ac.ir

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Abstract

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Abstract

An efficient approach is reported for the direct and sustainable construction of quinazolin-4(3H)-ones through a three-component reaction of isatoic anhydride, primary amines, and bromoacetyl bromide or chloroacetyl chloride in the presence of K₂CO₃ in DMSO. With bromoacetyl bromide, mono- or dibrominated quinazolinone scaffolds were obtainable in a chemo- and regioselective manner.

Key words

multicomponent reactions - quinazolinones - bromoacetyl bromide - regioselectivity - bromoquinazolines

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References

References and Notes

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14 Dibrominated 4(3H)-Quinazolinone 4aa–ah; General Procedure A mixture of isatoic anhydride (1; 1 mmol) and the appropriate primary amine 2 (1 mmol) in DMSO (3 mL) was stirred at 90 °C for 1 h. BrCH₂COBr (3a; 1 mmol) and K₂CO₃ (1 mmol) were added, and the mixture was stirred at 90 °C for a further 2 h. When the reaction was complete (TLC), the mixture was cooled to r.t. and the reaction was quenched with H₂O (3 mL). The mixture was then stirred for 10 min at r.t., and the resulting precipitate was collected by filtration, washed with H₂O, dried, and crystallized from EtOH. 3-Benzyl-6,8-dibromoquinazolin-4(3H)-one (4aa) White solid; yield: 0.374 g (95%); mp 173–175 °C (Lit.¹ 176.5–178.5 °C). IR (KBr): 1679 (C=O), 1596 (C=N), 1540, 1492, 1443, 1360, 1306, 1254, 1170, 1142, 1076, 1029, 996, 958, 875, 811, 723, 693, 670, 627 cm^–1. ¹H NMR (300.1 MHz, CDCl₃): δ = 5.21 (s, 2 H, CH₂), 7.37–7.41 (m, 5 H, 5CH), 8.16 (d, J = 2.1 Hz, 1 H, CH), 8.24 (s, 1 H, NCHN), 8.44 (d, J = 2.1, 1 H, CH). ¹³C NMR (75.5 MHz, CDCl₃): δ = 50.1 (CH₂), 120.8, 123.4 and 124.4 (3 C), 128.2 (2CH), 128.7 (CH), 129.2 (2CH and CH), 134.9 (C), 140.4 (CH), 144.7 (C), 147.3 (NCHN), 159.4 (C=O). EI-MS, m/z (%): 396 [M⁺, ⁸¹Br₂] (17), 394 [M⁺, ⁸¹Br⁷⁹Br] (35), 392 [M⁺, ⁷⁹Br₂] (19), 315 (4), 288 (4), 234 (4), 116 (1), 104 (1), 91 (100), 74 (3), 65 (14), 51 (3). Anal. Calcd for C₁₅H₁₀Br₂N₂O (394.06): C, 45.72; H, 2.56; N, 7.11. Found: C, 45.66; H, 2.43; N, 7.02.

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