Facile Synthesis of 4-Alkyl (and Aryl)-2-aryl-6-diazo-4<i>H</i>- thieno[3,2-<i>b</i>]pyridine-5,7-diones

Lee, Dong Joon; Kim, Kyongtae

doi:10.1021/jo049769a

Cited by 14 publications

(2 citation statements)

References 20 publications

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“…The corresponding thienopyrrole derivative 148 76 was also synthesized by application of the same methodology shown in Scheme 41 starting from 3-carboxythiophene-2acetic acid (147) (Scheme 42). 75 However, in this case the thiophene structure 148 was preserved; this is due to the increased aromatic character of the thiophene ring compared to furan.…”

Section: Figure 6 Structures Of Isomeric Furopyrrole Derivativesmentioning

confidence: 99%

Acyl Azides: Versatile Compounds in the Synthesis of Various Heterocycles

Balcı

2018

Synthesis

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Carbon–nitrogen bond formation is one of the most important reactions in organic chemistry. Various synthetic strategies for the generation of C–N bonds are described in the literature. For example, primary amines can be easily synthesized by the thermal decomposition of an acyl azide to an isocyanate, i.e. the Curtis rearrangement, followed by hydrolysis; the Curtius rearrangement has been used extensively. Furthermore, the advantage of the Curtius rearrangement is the isolation of acyl azides as well as the corresponding isocyanates. The isocyanates can be converted into various nitrogen-containing compounds upon reaction with various nucleophiles that can be used as important synthons for cyclization, in other words, for the synthesis of heterocycles. Therefore, this review demonstrates the importance of acyl azides not only in the synthesis acyclic systems, but also in the synthesis of various nitrogen-containing heterocycles.1 Introduction2 Synthesis of Acyl Azides2.1 Acyl Azides from Carboxylic Acid Derivatives2.2 Acyl Azides by Direct Transformation of Carboxylic Acids2.3 Acyl Azides from Aldehydes2.4 Carbamoyl Azides from Haloarenes, Sodium Azide, and N-Formylsaccharin3 Mechanism of Formation of Isocyanates4 Synthesis of Diacyl Azides5 Synthetic Applications5.1 Synthesis of Pyrimidinone Derivatives5.2 Dihydropyrimidinone and Isoquinolinone Derivatives5.3 Synthesis of Tetrahydroisoquinoline Skeleton5.4 Synthesis of Five-Membered Heterocycles5.5 Heterocycles Synthesized Starting from Homophthalic acid5.6 Heterocycles Synthesized from 2-(Ethoxycarbonyl)nicotinic Acid5.7 Formation of Aza-spiro Compounds5.8 Parham-Type Cyclization5.9 Diazepinone Derivatives5.10 Synthesis of Pyridine Derivatives5.11 Synthesis of Indole Derivatives6 Miscellaneous7 Conclusion

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Section: Figure 6 Structures Of Isomeric Furopyrrole Derivativesmentioning

confidence: 99%

Acyl Azides: Versatile Compounds in the Synthesis of Various Heterocycles

Balcı

2018

Synthesis

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“…However, in this case, the migration of the heteroatom does not take place in favor of the migration of alkyl 137b or aryl groups. 171 An interesting example is the preparation of b-lactams 203 on contraction of 3-diazopyrrolidine-2,4-diones 202, which can be prepared straightforwardly from a-amino esters (Scheme 54). However, in order for this reaction to occur, the a-amino esters must have a secondary amino group and the a position completely alkylated.…”

Section: Diazodiketonesmentioning

confidence: 99%