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Literature DB >> 21904417

Transannular Anti-Michael Addition: Formation of 4H-Pyrazolo[5,1-c]thiazines.

Yat Fan Suen¹, Håkon Hope, Michael H Nantz, Makhluf J Haddadin, And Mark J Kurth.

Abstract

The reaction of 2-(diphenylmethylene)thietan-3-one (2) with 1,2,4,5-tetrazines (3a-c) in KOH/MeOH/THF gives 4H-pyrazolo[5,1-c]thiazines (7a-c). This no vel condensation reaction proceeds via the intermediacy of an 8-(diphenylmethylene)-2H-1,4,5-thiadiazocin-7(8H)-one (5), which undergoes a multi-step rearrangement including a rare anti-Michael addition.

Entities: Chemical

Year: 2006 PMID： 21904417 PMCID： PMC3167077 DOI： 10.1016/j.tetlet.2006.09.015

Source DB: PubMed Journal: Tetrahedron Lett ISSN： 0040-4039 Impact factor: 2.415

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References

7 in total

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Authors: Yat Fan Suen; Håkon Hope; Michael H Nantz; Makhluf J Haddadin; Mark J Kurth
Journal: J Org Chem Date: 2005-10-14 Impact factor: 4.354

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Authors: S Peruncheralathan; T A Khan; H Ila; H Junjappa
Journal: J Org Chem Date: 2005-11-25 Impact factor: 4.354

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Authors: M J Genin; C Biles; B J Keiser; S M Poppe; S M Swaney; W G Tarpley; Y Yagi; D L Romero
Journal: J Med Chem Date: 2000-03-09 Impact factor: 7.446

Transannular Anti-Michael Addition: Formation of 4H-Pyrazolo[5,1-c]thiazines.

1. Synthesis and biological evaluation of the 1,5-diarylpyrazole class of cyclooxygenase-2 inhibitors: identification of 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benze nesulfonamide (SC-58635, celecoxib).

2. A novel route to fully substituted 1H-pyrazoles.

3. Regioselective synthesis of 1-aryl-3,4-substituted/annulated-5-(methylthio)pyrazoles and 1-aryl-3-(methylthio)-4,5-substituted/annulated pyrazoles.

4. Novel 1,5-diphenylpyrazole nonnucleoside HIV-1 reverse transcriptase inhibitors with enhanced activity versus the delavirdine-resistant P236L mutant: lead identification and SAR of 3- and 4-substituted derivatives.

5. Selective transannular ring transformations in azirino-fused eight-membered O,N- or S,N-heterocycles.

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7. Diazocinones: synthesis and conformational analysis.