Microwave Assisted Synthesis of 2,2'-Arylene-substituted Bis(4H-3,1-Benzoxazin-4-one) Derivatives Using the Complex Cyanuric Chloride/N,N-Dimethylformamide
Abstract
:1. Introduction
2. Results and Discussion
3. Experimental
3.1. General
3.2. Preparation of 2,2′-(1,4-Phenylene)bis(4H-3,1-benzoxazin-4-one) (A1)
3.2.1. Step 1: Preparation of 2,2′-[1,4-Phenylene-bis(carbonylimino)]dibenzoic Acid
3.2.2. Step 2: Reaction of 2,2′-[1,4-Phenylene-bis(carbonylimino)]dibenzoic Acid with CC/DMF
3.3. Preparation of 2,2′-(1,4-Naphthylene)bis(4H-3,1-benzoxazin-4-one) (A2)
3.3.1. Step 1: Preparation of 2,2′-[1,4-Naphthylene-bis (carbonylimino)] Dibenzoic Acid
3.3.2. Step 2: Reaction of 2,2′-[1,4-Naphthylene-bis (carbonylimino)] Dibenzoic Acid with CC/DMF
3.4. Preparation of 2,2′-(4,4′-Biphenylene)bis(4H-3,1-benzoxazin-4-one) (A3)
3.4.1. Step 1: Preparation of 2,2′-[4,4′-Biphenylene-bis(carbonylimino)]dibenzoic Acid
3.4.2. Step 2: Reaction of 2,2′-[4,4′-Biphenylene-bis(carbonylimino)]dibenzoic Acid with CC/DMF
3.5. Preparation of 2,2′-(2,7-Naphthylene)bis(4H-3,1-benzoxazin-4-one) (A4)
3.5.1. Step1: Preparation of 2,2′-[2,7-Naphthylene-bis(carbonylimino)]dibenzoic Acid
3.5.2. Step 2: Reaction of 2,2′-[2,7-Naphthylene-bis(carbonylimino)]dibenzoic Acid with CC/DMF
3.6. Preparation of 2,2′-(1,4-Phenylene)bis(5,7-dichloro-4H-3,1-benzoxazin-4-one) (A5)
3.6.1. Step 1: Preparation of 2,2′-[1,4-Phenylene-bis (carbonylimino)]bis(4,6-dichlorobenzoic acid)
3.6.2. Step 2: Reaction of 2,2′-[1,4-Phenylene-bis (carbonylimino)]bis(4,6-dichlorobenzoic acid) with CC/DMF
4. Conclusions
Acknowledgments
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Sample Availability: Samples of the compounds A1–5 and B1–5 are available from the authors. |
Name and Structure | Product | Yield (%) | Time (min) | M.p. (°C) |
---|---|---|---|---|
A1 | 88 | 1 | 314–316 | |
A2 | 85 | 1.5 | 268–270 | |
A3 | 85 | 1.5 | 376–378 | |
A4 | 79 | 2 | 278–280 | |
A5 | 77 | 2 | 325–327 |
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Shariat, M.; Samsudin, M.W.; Zakaria, Z. Microwave Assisted Synthesis of 2,2'-Arylene-substituted Bis(4H-3,1-Benzoxazin-4-one) Derivatives Using the Complex Cyanuric Chloride/N,N-Dimethylformamide. Molecules 2012, 17, 11607-11615. https://doi.org/10.3390/molecules171011607
Shariat M, Samsudin MW, Zakaria Z. Microwave Assisted Synthesis of 2,2'-Arylene-substituted Bis(4H-3,1-Benzoxazin-4-one) Derivatives Using the Complex Cyanuric Chloride/N,N-Dimethylformamide. Molecules. 2012; 17(10):11607-11615. https://doi.org/10.3390/molecules171011607
Chicago/Turabian StyleShariat, Mehdi, Mohd Wahid Samsudin, and Zuriati Zakaria. 2012. "Microwave Assisted Synthesis of 2,2'-Arylene-substituted Bis(4H-3,1-Benzoxazin-4-one) Derivatives Using the Complex Cyanuric Chloride/N,N-Dimethylformamide" Molecules 17, no. 10: 11607-11615. https://doi.org/10.3390/molecules171011607