Bridgehead nitrogen heterocycles. IX. Fused-ring systems derived from fusion of the 1,2,4-thiadiazole system with the isoxazole, 1,3,4-oxadiazole, thiazole, 1,2,4-thiadiazole, and 1,3,4-thiadiazole systems

K. T. Potts; J. Kane

doi:10.1021/jo00906a006

Bridgehead nitrogen heterocycles. IX. Fused-ring systems derived from fusion of the 1,2,4-thiadiazole system with the isoxazole, 1,3,4-oxadiazole, thiazole, 1,2,4-thiadiazole, and 1,3,4-thiadiazole systems

The Journal of Organic Chemistry ◽

10.1021/jo00906a006 ◽

1975 ◽

Vol 40 (18) ◽

pp. 2600-2604 ◽

Cited By ~ 17

Author(s):

K. T. Potts ◽

J. Kane

Keyword(s):

Nitrogen Heterocycles ◽

Ring Systems ◽

Fused Ring ◽

Bridgehead Nitrogen

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ChemInform Abstract: BRIDGEHEAD NITROGEN HETEROCYCLES PART 9, FUSED-RING SYSTEMS DERIVED FROM FUSION OF THE 1,2,4-THIADIAZOLE SYSTEM WITH ISOXAZOLE, 1,3,4-OXADIAZOLE, THIAZOLE, 1,2,4-THIADIAZOLE, AND 1,3,4-THIADIAZOLE SYSTEMS

Chemischer Informationsdienst ◽

10.1002/chin.197550213 ◽

1975 ◽

Vol 6 (50) ◽

pp. no-no

Author(s):

K. T. POTTS ◽

J. KANE

Keyword(s):

Nitrogen Heterocycles ◽

Ring Systems ◽

Fused Ring ◽

Bridgehead Nitrogen

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The Chemistry of Sulfur-Containing [5,5]-Fused Ring Systems With a Bridgehead Nitrogen

Advances in Heterocyclic Chemistry ◽

10.1016/bs.aihch.2017.10.003 ◽

2018 ◽

pp. 301-356 ◽

Cited By ~ 3

Author(s):

Frédéric Buron ◽

Marie-Aude Hiebel ◽

Jean-Yves Mérour ◽

Karen Plé ◽

Sylvain Routier

Keyword(s):

Ring Systems ◽

Fused Ring ◽

Bridgehead Nitrogen ◽

Sulfur Containing

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Electronic structure and spectra of fused n/m ring systems with one or two bridgehead nitrogen atoms—IV

Tetrahedron ◽

10.1016/s0040-4020(01)82774-5 ◽

1969 ◽

Vol 25 (10) ◽

pp. 2259-2264 ◽

Cited By ~ 7

Author(s):

V. Galasso ◽

G. De Alti

Keyword(s):

Electronic Structure ◽

Ring Systems ◽

Bridgehead Nitrogen

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ChemInform Abstract: Bridgehead Nitrogen Heterocycles. Part 4. Reactions of 3-Acyl/Aroyl-5-(2,4-dichlorophenyl)-1,3,4-oxadiazol-2(3H)-ones with Diamines.

ChemInform ◽

10.1002/chin.199132189 ◽

2010 ◽

Vol 22 (32) ◽

pp. no-no

Author(s):

P. C. GOGOI ◽

J. C. S. KATAKY

Keyword(s):

Nitrogen Heterocycles ◽

Bridgehead Nitrogen

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ChemInform Abstract: Synthesis and Biological Activity of Bridgehead Nitrogen Heterocycles.

ChemInform ◽

10.1002/chin.198725140 ◽

1987 ◽

Vol 18 (25) ◽

Author(s):

B. N. GOSWAMI ◽

J. C. S. KATAKY ◽

J. N. BARUAH

Keyword(s):

Biological Activity ◽

Nitrogen Heterocycles ◽

Bridgehead Nitrogen

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Synthesis of Pyrazolofuropyrazine via One-Pot SNAr Reaction and Intramolecular Direct C–H Arylation

Synthesis ◽

10.1055/s-0036-1591885 ◽

2018 ◽

Vol 50 (07) ◽

pp. 1493-1498 ◽

Cited By ~ 3

Author(s):

Shinichiro Fuse ◽

Hiroyuki Nakamura ◽

Megumi Inaba ◽

Shinichi Sato ◽

Manjusha Joshi

Keyword(s):

Drug Discovery ◽

Rapid Development ◽

Ring System ◽

Biologically Active ◽

Drug Candidate ◽

One Pot ◽

Ring Systems ◽

Drug Candidates ◽

Fused Ring ◽

Snar Reaction

Fused-ring systems containing heterocycles are attractive templates for drug discovery. Biologically active 6-5-5+6 fused-ring systems that possess heterocycles are available, but these require a relatively large number of synthetic steps for preparation. Therefore, pyrazolofuropyrazine was designed as a 6-5-5+6 ring system template that incorporates ready accessibility for drug discovery. Pyrazolofuropyrazines were successfully constructed in only a few steps via one-pot SNAr reaction/intramolecular C–H direct arylation. As a drug candidate, pyrazolofuropyrazine has earned a favorable LogP, although significant biological activity has yet to be established; the ready accessibility of pyrazolofuropyrazine template, however, offers an opportunity for the rapid development of promising new drug candidates.

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