Synthesis of different types of valerolactams starting from 2,5-dihydrooxazoles

Johannes, Katharina; Martens, Jürgen

doi:10.1016/j.tet.2009.10.107

Cited by 19 publications

(13 citation statements)

References 44 publications

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“…图式 7 硫代水杨酸与席夫碱的反应 Scheme 7 Reaction of thiosalicylic acid with schiff base 2010 年, Martens 等 [32] 利用硫代水杨酸和环状亚胺衍生物为原料, 在甲苯中回流首先得到了巯基与亚胺发生加成反应的中间体 14 [33] , 然后脱水环化合成 1,3-苯并噻嗪-4-酮类衍生物, 总产率 27%～74% (Scheme 9 率高达 96% (Scheme 11). 此法是一步合成 1,3-苯并噻嗪二酮的好方法, 在文中没有讨论该方法的反应机理, 我们认为巯基与羧基可能均与异氰酸酯反应生成了中间体 20 [35] , 然后环化合成了目标产物.…”

Section: 分子内成环合成 13-苯并噻嗪酮的方法unclassified

Review About the Synthesis of 1,3-Benzothiazinone Derivatives

李闪闪¹,

Shanshan²

2016

Chin. J. Org. Chem.

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1,3-Benzothiazinone derivatives have widely bioactivities. So the methods for the synthesis of these 1,3-benzothiazinone derivatives have attracted enormous attentions worldwide. From the method of introducing sulfur atom and the reaction mechanism for the formation of benzothiazinone derivatives, the method of synthesizing 1,3-benzothiazinone derivatives has been summarized in this review. So the thiophenol derivatives, disulfide derivatives, the same carbon connected with amino and mercapto derivatives, isothiocyanate derivatives and some smaller sulfur molecules are used as starting materials.

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Section: 分子内成环合成 13-苯并噻嗪酮的方法unclassified

Review About the Synthesis of 1,3-Benzothiazinone Derivatives

李闪闪¹,

Shanshan²

2016

Chin. J. Org. Chem.

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“…The characteristic attribute of the 2,5-dihydro- (Tables 3 and 4). Due attention needs to be paid to the fact that the configuration at the existing stereogenic center of the imines can influence the formation of the new chirality center formed in the reaction [18,38].…”

Section: Conversion Of the 25-dihydro-13-thiazoles Into On-diacyl mentioning

confidence: 99%

“…The reason for this reaction course is the bulkiness of the phenyl group. The likewise voluminous carboxylate avoids the bulky phenyl group [18,38] and attacks from the less hindered side resulting predominantly in trans-configurated amides 3. On the other hand, the attack of the carboxylate on the N-acyliminium ions occurs cis to the tert-butyl group during the reaction to O,N-diacyl O,N-acetals 4 (Fig.…”

Section: Conversion Of the 25-dihydro-13-thiazoles Into On-diacyl mentioning

confidence: 99%

“…On account of this, the direct influence on the creation of the new stereogenic center is less important. In fact, the bulky tert-butyl group displaces the amido moiety to the opposite site [18,38]. The attack of the carboxylate occurs, therefore, evasively on the amido moiety leading predominantly to cis-configurated O,N-diacyl O,N-acetals 4.…”

Section: Conversion Of the 25-dihydro-13-thiazoles Into On-diacyl mentioning

confidence: 99%

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2,5-Dihydro-1,3-thiazoles as Scaffolds in the Synthesis of O,N-Diacyl O,N-Acetals in a One-pot Reaction

Stalling

Brockmeyer

Kröger

et al. 2012

Zeitschrift Für Naturforschung B

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The Asinger reaction is a very powerful tool to form 2,5-dihydro-1,3-thiazoles in high yields. Treating these heterocyclic imines with acid chlorides followed by adding sodium carboxylates led to a large number of new O,N-diacyl O,N-acetals. Using chiral starting materials, a high diastereoselectivity was observed in several cases. X-Ray structures document the constitution and clarify the relative configuration of the prepared O, N-diacyl O,N-acetals.

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“…图式 1 喹唑啉-4-酮的合成方法 Scheme 1 Synthetic protocols for quinazolin-4(3H)-one 唑啉-4-酮衍生物 [9] . 由于邻氨基苯甲酸中氨基的亲核性较弱, 使得氨基直接对亚胺的亲核加成难以发生.…”

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Synthesis and Anti-tumor Activity of Novel Quinazolin-4-one Derivatives

孙佳婧¹,

周利凯²,

谭官海³

et al. 2017

Chin. J. Org. Chem.

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A series of novel C-2 and N-3 disubstituted quinazolin-4(3H)-one derivatives 5 possessing amino acid chain were synthesized by the addition reaction of imine with iminoketene and aromatization using anthranilic acid, aromatic aldehyde and glycine ethyl ester as starting materials. After elimination of carboxymethyl in the acidic condition, novel quinazolin-4(3H)-one derivatives 9 bearing amino side chain were designed and synthesized by SN2 substitution reaction. The compounds were evaluated for their anti-proliferation activities against four tumor cells. The results showed that some of the compounds, such as 9ba and 9bc showed significantly anti Hela activity with the IC 50 values of 8.16 μM and 7.47 μM, respectively, while 9bc and 9bd against A549 with the IC 50 values of 5.62 μM and 9.54 μM, respectively. Structure activity relationship analysis of these analogues suggested that coumarin substituent (extended π planar aromatic ring) on C-2 position and the introduction of amino side chain should be favorable to their anti-tumor activities.

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Synthesis of different types of valerolactams starting from 2,5-dihydrooxazoles

Cited by 19 publications

References 44 publications

Review About the Synthesis of 1,3-Benzothiazinone Derivatives

Review About the Synthesis of 1,3-Benzothiazinone Derivatives

2,5-Dihydro-1,3-thiazoles as Scaffolds in the Synthesis of O,N-Diacyl O,N-Acetals in a One-pot Reaction

Synthesis and Anti-tumor Activity of Novel Quinazolin-4-one Derivatives

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