Transannular anti-Michael addition: formation of 4H-pyrazolo[5,1-c]thiazines

Yat Fan Suen; Håkon Hope; Michael H. Nantz; Makhluf J. Haddadin; Mark J. Kurth

doi:10.1016/j.tetlet.2006.09.015

Transannular anti-Michael addition: formation of 4H-pyrazolo[5,1-c]thiazines

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

Chemistry

Research output: Contribution to journal › Article › peer-review

9 Scopus citations

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 novel 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.

Original language	English (US)
Pages (from-to)	7893-7896
Number of pages	4
Journal	Tetrahedron Letters
Volume	47
Issue number	45
DOIs	https://doi.org/10.1016/j.tetlet.2006.09.015
State	Published - Nov 6 2006

Keywords

4H-Pyrazolo[5,1-c]thiazine
Anti-Michael addition
Pyrazole

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Drug Discovery

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title = "Transannular anti-Michael addition: formation of 4H-pyrazolo[5,1-c]thiazines",

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 novel 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.",

keywords = "4H-Pyrazolo[5,1-c]thiazine, Anti-Michael addition, Pyrazole",

author = "Suen, {Yat Fan} and H{\aa}kon Hope and Nantz, {Michael H.} and Haddadin, {Makhluf J.} and Kurth, {Mark J.}",

year = "2006",

month = nov,

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doi = "10.1016/j.tetlet.2006.09.015",

language = "English (US)",

volume = "47",

pages = "7893--7896",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Transannular anti-Michael addition

T2 - formation of 4H-pyrazolo[5,1-c]thiazines

AU - Suen, Yat Fan

AU - Hope, Håkon

AU - Nantz, Michael H.

AU - Haddadin, Makhluf J.

AU - Kurth, Mark J.

PY - 2006/11/6

Y1 - 2006/11/6

N2 - 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 novel 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.

AB - 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 novel 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.

KW - 4H-Pyrazolo[5,1-c]thiazine

KW - Anti-Michael addition

KW - Pyrazole

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JO - Tetrahedron Letters

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