Preparation of New Nitrogen-Bridged Heterocycles. XXXIII. A New Preparative Method for Thieno(3,2-a)indolizines.

Kakehi, Akikazu; Ito, Suketaka; Ueda, Tatsuya; Takano, Satoshi

doi:10.1248/cpb.41.1753

Cited by 5 publications

(1 citation statement)

References 2 publications

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“…72 Subsequent re-alkylation of the sulfur atom under basic conditions regenerates the a,b-unsaturated nitrile 151. 73 When a suitable alkylating agent is used (R 2 = EWG), a Michael addition of the in situ generated anion occurs to dihydrothiophene 152, which aromatizes to thiophene 150 by the elimination of ethyl-2-cyanoacetate.…”

Section: Ring Transformationsmentioning

confidence: 99%

Synthesis of isoindoles and related iso-condensed heteroaromatic pyrroles

2012

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Over the past few years, isoindoles have found wide application in materials science. Isoindole containing BODIPY dyes are highly fluorescent materials and have been extensively used in various fields of science. Phthalocyanines, metal containing cyclic tetramers of isoindole, form coordination complexes with most elements of the periodic table. These complexes are intensely coloured and are used as pigments and dyes. However, isoindoles are relatively unstable 10π-heteroaromatic systems and few synthetic methods provide these compounds in good yields. This tutorial review will give an overview of the reported synthetic methods towards isoindoles and related heteroaromatic systems over a time span of approximately 10 years (2000 to current), including the applications where they have been reported. The importance of the field will be illustrated and factors influencing product stability will be discussed.

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Section: Ring Transformationsmentioning

confidence: 99%

Synthesis of isoindoles and related iso-condensed heteroaromatic pyrroles

2012

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ChemInform Abstract: Preparation of New Nitrogen‐Bridged Heterocycles. Part 33. A New Preparative Method for Thieno(3,2‐a)indolizines.

et al. 1994

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Preparation of New Nitrogen-Bridged Heterocycles. Part 33. A New Preparative Method for Thieno(3,2-a)indolizines.-Treatment of (I) with tBu-OK causes ring opening and formation of 2-indolizinethiolates, which undergo alkylation to give the S-alkylated 1-vinylindolizines (III). 2-Acetonylthio-and 2-phenacylthio derivatives of these products undergo an intramolecular Michael addition to afford the thieno(3,2-a)indolizines (V) with elimination of a methylene compound. -(KAKEHI, A.; ITO, S.; UEDA, T.; TAKANO, S.; Chem.

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Three Heterocyclic Rings Fused (5-5-6)

Riggs

Smith²

2008

Comprehensive Heterocyclic Chemistry III

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Preparation of New Nitrogen-Bridged Heterocycles. XXXIII. A New Preparative Method for Thieno(3,2-a)indolizines.

Cited by 5 publications

References 2 publications

Synthesis of isoindoles and related iso-condensed heteroaromatic pyrroles

Synthesis of isoindoles and related iso-condensed heteroaromatic pyrroles

ChemInform Abstract: Preparation of New Nitrogen‐Bridged Heterocycles. Part 33. A New Preparative Method for Thieno(3,2‐a)indolizines.

Three Heterocyclic Rings Fused (5-5-6)

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