Heterocyclic derivatives of 1 : 2-5 : 6-dibenzocyclohepta-1 : 3 : 5-triene. Part II. 5-Aryl-2 : 3-6 : 7-dibenzo-1-thia-4-azacyclohepta-2 : 4 : 6-trienes and their 1 : 1-dioxides

Brodrick, C. I.; Nicholson, Judith; Short, W. F.

doi:10.1039/jr9540003857

Cited by 9 publications

(3 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…However, only a few studies have been directed to the synthesis of tricyclic benzothiazepines. Brodrock et al reported a Bischler−Napieralski-type cyclization of 2-benzamidodiaryl sulfides in the preparation of dibenzothiazepines . Subsequently, Hunziker extended the methodology to other dibenzothiazepine derivatives .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel Tricyclic Pyrimido[4,5-b][1,4]benzothiazepines via Bischler−Napieralski-Type Reactions

Dang

et al. 2005

J. Org. Chem.

View full text Add to dashboard Cite

[reaction: see text] Novel tricyclic pyrimido[4,5-b][1,4]benzothiazepines were readily prepared from 5-amino-4,6-bis(arylthio)pyrimidines and carboxylic acids via Bischler-Napieralski-type reactions. The 6-aryl sulfide group of the resulting pyrimido[4,5-b][1,4]benzothiazepines could be selectively oxidized to its corresponding sulfoxide, which underwent facile substitution reactions when treated with nucleophiles such as an amine. This synthetic strategy provides an efficient way to access a library of novel heterocyclic compounds that are of interest in drug discovery.

show abstract

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel Tricyclic Pyrimido[4,5-b][1,4]benzothiazepines via Bischler−Napieralski-Type Reactions

Dang

et al. 2005

J. Org. Chem.

View full text Add to dashboard Cite

show abstract

“…Step 2: Crude 3-aminopyridine-2-thiol (7), 2-fluorobenzaldehyde (8; 5 mmol, 621 mg), and K 2 CO 3 (5 mmol, 0.690 g) were added to polyethylene glycol (20 mL), and the mixture was heated at 100 °C for 6 h. After the reaction mixture was cooled to rt, H2O (150 mL) was added. The crude product was extracted with EtOAc, washed with brine (2 ×), dried (anhyd Na 2 SO 4 ), evaporated and the crude was purified by column chromatography on silica gel (PE/EtOAc 5:1 v/v, 2% of Et 3 N) delivering benzo[f]pyrido [2,3-b] [1,4]thiazepine (9); yellow solid; yield: 424 mg (40% over 2 steps).…”

Section: Total Synthesis Of H460 Taxr Inhibitormentioning

confidence: 99%

“…Generally, the existing methods for preparing these compounds are mainly based on a multistep linear synthesis (Scheme 1a), in which the aryl groups are mainly introduced by the original aroyl-bearing substrates and the C=N bond is formed in the final step. [8][9][10][11][12][13][14] This strategy always causes synthetic dilemmas, if products with different 11-aryls are wanted, chemists will be forced to repeat the multi-step synthetic sequence for each of target products. As a consequence, the synthetic efficiency cannot be well secured.…”

mentioning

confidence: 99%

Late-Stage Two-Step C11–H Arylation of Dibenzooxa/thiazepines

Yang¹,

et al. 2023

Synthesis

View full text Add to dashboard Cite

A practical and efficient synthesis of 11-aryldibenzooxa/thiazepines is achieved, via a late-stage and two-step C11-H arylation of simple dibenzooxa/thiazepines. The adoption of Grignard addition and DDQ dehydrogenation allows for opera-tionally simple and chemically reliable, and step-efficient and high-yielding transformations. The two-step and one-pot procedures provide excellent yields. The gram-scale experiment demonstrates the promising synthetic potentials in large-scale applications, and the advantages of this method are also highlighted in the efficient synthesis of an H460TaxR inhibitor.

show abstract

Extrusion Reactions Affording Aromatic Systems, Dienes and Polyenes

Guziec

2022

Organic Reactions

View full text Add to dashboard Cite

Extrusion reactions may be defined as chemical reactions in which an atom or small molecular fragment Y connected to two other atoms W and Z is lost from a molecule, leading to a product in which W becomes directly bonded to Z. Cheletropic reactions that afford aromatic or conjugated π systems by loss of a stable atomic or molecular fragment have also been classified as extrusion reactions. Typically, the fragments liberated in these reactions are small, stable inorganic molecules or atoms such as carbon monoxide, carbon dioxide, sulfur, sulfur monoxide, sulfur dioxide, selenium, tellurium, oxygen and nitrogen. This chapter primarily deals with the synthesis of arenes, heterocycles, 1,3‐dienes and polyenes using such extrusion processes. The utility of these reactions in the synthesis of sterically hindered molecules, dendrimers, pheromones, and other natural products are highlighted. The use of extrusion reactions for the “Click and Release” approach in drug development is also introduced.

show abstract

Heterocyclic derivatives of 1 : 2-5 : 6-dibenzocyclohepta-1 : 3 : 5-triene. Part II. 5-Aryl-2 : 3-6 : 7-dibenzo-1-thia-4-azacyclohepta-2 : 4 : 6-trienes and their 1 : 1-dioxides

Cited by 9 publications

References 0 publications

Synthesis of Novel Tricyclic Pyrimido[4,5-b][1,4]benzothiazepines via Bischler−Napieralski-Type Reactions

Synthesis of Novel Tricyclic Pyrimido[4,5-b][1,4]benzothiazepines via Bischler−Napieralski-Type Reactions

Late-Stage Two-Step C11–H Arylation of Dibenzooxa/thiazepines

Extrusion Reactions Affording Aromatic Systems, Dienes and Polyenes

Contact Info

Product

Resources

About