| Reference | [1]. Kobayashi, K., Hashimoto, H., Kanbe, Y. and Konishi, H., 2011.<br />
One-pot synthesis of 4-substituted 4-alkoxy-1, 4-dihydro-3, 1-benzoxazine-2-thiones by the reaction of 2-isothiocyanatobenzoates with organolithiums.<br />
Abstract: An efficient one-pot procedure for the preparation of 4-substituted 4-alkoxy-1,4-dihydro-3,1-benzoxazine-2-thiones from 2-isothiocyanatobenzoates has been developed. Thus, 2-isothiocyanatobenzoates were reacted with organolithiums including lithium enolates of acetates and tertiary acetamides in THF at −78 °C to give the desired products in generally good yields.<br />
Tetrahedron, 67(25), pp.4535-4538.<br />
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[2]. Wulan, F.F., Wahyuningsih, T.D., Jumina, J. and Kumar, N., 2021.<br />
Synthesis Studies of N-Acetyl Glyoxylamide Derivatives Using Unreactive Amines.<br />
Abstract: This research was performed to synthesize the glyoxylamide made from N-acetylisatin and anthranilic acid derivatives. The synthesis was conducted in two steps, starting from the formation of glyoxylamide using N-acetylisatin and methyl anthranilate as the starting material. The reaction was performed under reflux and inert nitrogen gaseous atmosphere for 48 h in the presence of DIPEA in acetonitrile (ACN) solvent. However, that reaction has proven to be unsuccessful. Several strategies were performed to increase the ease of glyoxylamide syntheses, such as increasing the electrophilicity of the isatin ring and increasing the nucleophilicity of the amine. The methyl anthranilate derivatives, methyl-2-amino-5-methoxybenzoate, and methyl-2-amino-4-methoxybenzoate has already been used and proven to be success to ring open the N-acetylisatin and produced glyoxylamide 5 and 6 with a yield of 12% and 11%, respectively. Thus, the desired benzoic acid functional group obtained from the hydrolysis of 5 and 6 successfully produced glyoxylamide 7 and 8 with a yield of 52% and 42%, respectively.<br />
In Key Engineering Materials (Vol. 884, pp. 312-319). Trans Tech Publications Ltd.<br />
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[3]. Reddy, C.R. and Sinare, S.N., 2020.<br />
Expedient Approach to the Synthesis of Betrixaban.<br />
Abstract A new scalable route to synthesize the factor Xa (FXa) inhibitor betrixaban is disclosed. The product is obtained in a seven-step reaction sequence (in five stages using two one-pot reactions) starting from easily accessible 4-(N,N-dimethylcarbamimidoyl)benzoate. Effective isolation of intermediates, use of cost-effective amide formation and 2-methyltetrahydrofuran as an effective reaction solvent as well as for extraction in three of the stages, are key features. The strategy provides the desired product in 38% overall yield with high purity (>98%).<br />
SynOpen, 4(03), pp.62-65.<br />
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[4]. Norris, R.K. and Sternhell, S., 1972.<br />
3-Substituted 1, 4-Benzoquinone 4-oximes.<br />
Abstract: The preparation and physical properties of seven compounds in the title series are described. When the 3-substituent is F, Cl, Br, I, Me, or OMe the compounds exist predominantly (>95%) in the oxime form. The 3-methoxy-carbonyl derivative is estimated to exist in the nitroso form to the extent of 23%.<br />
Australian Journal of Chemistry, 25(12), pp.2621-2629.<br />
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[5]. Wang, Y.W., Zheng, L., Jia, F.C., Chen, Y.F. and Wu, A.X., 2019.<br />
Oxidative ring-opening of isatins for the synthesis of 2-aminobenzamides and 2-aminobenzoates.<br />
Abstract: An efficient and practical isatin-based oxidative domino protocol has been developed for the facile synthesis of 2-aminobenzamides and 2-aminobenzoates. The robust nature of this reaction system is reflected by accessible starting materials, room temperature and high-yield gram-scale synthesis.<br />
Tetrahedron, 75(11), pp.1497-1503.
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