e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

The intramolecular nitrene type 1, 1-cycloaddition reaction of allyl-substituted diazomethanes

T Miyashi, Y Nishizawa, Y Fujii…

Index: Miyashi,T.; Nishizawa,Y.; Fujii,Y. Journal of the American Chemical Society, 1986 , vol. 108, p. 1617

Full Text: HTML

Citation Number: 25

Abstract

Abstract: Various allyl-substituted diazomethanes generated by pyrolyses of the sodium salts of corresponding tosylhydrazones undergo a reversible intramolecular nitrene-type 1, I- cycloaddition to give 1, 2-diazabicyclo [3.1. O] hex-2-enes. Stereochemical results obtained from (E)-and (Z)-5-phenyl-5-diazopent-2-enes,(E)-1, 4-diphenyl-4-diazobut-l-ene, and (Z)-3- methyl-6-aryl-6-diazohex-3-enes indicated that both the 1, I-and retro-l, I-cycloaddition ...

3,4-Dihydronaphthalen-1(2H)-one Structure

3,4-Dihydronaph...

~%

ethyl 2-(3,4-dihydronaphthalen-1-yl)acetate Structure

ethyl 2-(3,4-di...

1-Naphthaleneacetic acid, 1,2,3,4-tetrahydro-1-hydroxy-, ethyl ester Structure

1-Naphthaleneac...

~%

1,2,3,4-tetrahydronaphthalen-1-ylidine acetatic acid ethyl ester Structure

1,2,3,4-tetrahy...

ethyl 2-(3,4-dihydronaphthalen-1-yl)acetate Structure

ethyl 2-(3,4-di...

Ethyl (1-hydroxycyclopentyl)acetate Structure

Ethyl (1-hydrox...

~20%

Ethyl 1-Cyclopentene-1-Carboxylate Structure

Ethyl 1-Cyclope...

ethyl 2-cyclopentylideneacetate Structure

ethyl 2-cyclope...

ethyl cyclopent-1-ene-1-acetate Structure

ethyl cyclopent...

sodium salt of (Z)-1-phenyl-3-penten-1-one N-tosylhydrazone Structure

sodium salt of ...

~0%

Sodium toluene-4-sulphinate Structure

Sodium toluene-...

3-phenyl-6-endo-ethyl-6-exo-methyl-1,2-diazabicyclo[3.1.0]hex-2-ene Structure

3-phenyl-6-endo...

sodium salt of 1-(p-bromophenyl)-4-methyl-3-penten-1-one N-tosylhydrazone Structure

sodium salt of ...

~0%

Sodium toluene-4-sulphinate Structure

Sodium toluene-...

3-(p-bromophenyl)-6,6-dimethyl-1,2-diazabicyclo(3.1.0)hex-2-ene Structure

3-(p-bromopheny...

sodium salt of 1-(p-chlorophenyl)-4-methyl-3-penten-1-one N-tosylhydrazone Structure

sodium salt of ...

~0%

Sodium toluene-4-sulphinate Structure

Sodium toluene-...

3-(p-chlorophenyl)-6,6-dimethyl-1,2-diazabicyclo(3.1.0)hex-2-ene Structure

3-(p-chlorophen...

sodium salt of α-(cyclopenten-1-yl)acetophenone N-tosylhydrazone Structure

sodium salt of ...

~0%

2-phenyl-4a,5,6,7-tetrahydro-1H-cyclopenta[2,3]azirino[1,2-b]pyrazole Structure

2-phenyl-4a,5,6...

Sodium toluene-4-sulphinate Structure

Sodium toluene-...

sodium salt of (Z)-(p-bromophenyl)-4-methyl-3-hexen-1-one N-tosylhydrazone Structure

sodium salt of ...

~0%

Sodium toluene-4-sulphinate Structure

Sodium toluene-...

3-(p-bromophenyl)-6-endo-ethyl-6-exo-methyl-1,2-diazabicyclo[3.1.0]hex-2-ene Structure

3-(p-bromopheny...

sodium salt of (E)-1,6-diphenyl-5-hexen-1-one N-tosylhydrazone Structure

sodium salt of ...

~0%

Sodium toluene-4-sulphinate Structure

Sodium toluene-...

3,6a-diphenyl-3,3a,4,5,6,6a-hexahydrocyclopenta[c]pyrazole Structure

3,6a-diphenyl-3...

sodium salt of 1-phenyl-4-methyl-3-penten-1-one N-tosylhydrazone Structure

sodium salt of ...

~0%

3-phenyl-6,6'-dimethyl-1,2-diazabicyclo[3.1.0]hex-2-ene Structure

3-phenyl-6,6'-d...

Sodium toluene-4-sulphinate Structure

Sodium toluene-...

sodium salt of 1-(p-tolyl)-4-methyl-3-penten-1-one N-tosylhydrazone Structure

sodium salt of ...

~0%

Sodium toluene-4-sulphinate Structure

Sodium toluene-...

3-(p-tolyl)-6,6-dimethyl-1,2-diazabicyclo(3.1.0)hex-2-ene Structure

3-(p-tolyl)-6,6...

sodium salt of 1-(p-anisyl)-4-methyl-3-penten-1-one N-tosylhydrazone Structure

sodium salt of ...

~0%

Sodium toluene-4-sulphinate Structure

Sodium toluene-...

3-(p-anisyl)-6,6-dimethyl-1,2-diazabicyclo(3.1.0)hex-2-ene Structure

3-(p-anisyl)-6,...

sodium salt of 1-(p-cyanophenyl)-4-methyl-3-penten-1-one N-tosylhydrazone Structure

sodium salt of ...

~0%

Sodium toluene-4-sulphinate Structure

Sodium toluene-...

3-(p-cyanophenyl)-6,6-dimethyl-1,2-diazabicyclo[3.1.0]hex-2-ene Structure

3-(p-cyanopheny...

sodium salt of 1-(m-nitrophenyl)-4-methyl-3-penten-1-one N-tosylhydrazone Structure

sodium salt of ...

~0%

Sodium toluene-4-sulphinate Structure

Sodium toluene-...

3-(m-nitrophenyl)-6,6-dimethyl-1,2-diazabicyclo[3.1.0]hex-2-ene Structure

3-(m-nitropheny...

sodium salt of (E)-1,4-diphenyl-3-buten-1-one N-tosylhydrazone Structure

sodium salt of ...

~0%

trans-1,4-diphenyl-4-diazobut-1-ene Structure

trans-1,4-diphe...

Sodium toluene-4-sulphinate Structure

Sodium toluene-...

(5R,6R)-3,6-diphenyl-1,2-diazabicyclo[3.1.0]hex-2-ene Structure

(5R,6R)-3,6-dip...

sodium salt of (Z)-1-phenyl-3-penten-1-one N-tosylhydrazone Structure

sodium salt of ...

~0%

Sodium toluene-4-sulphinate Structure

Sodium toluene-...

(Z)-(1-diazopent-3-en-1-yl)benzene Structure

(Z)-(1-diazopen...

exo-3-phenyl-6-methyl-1,2-diazabicyclo[3.1.0]hex-2-ene Structure

exo-3-phenyl-6-...

Detail

trans-1,4-diphenyl-4-diazobut-1-ene Structure

trans-1,4-diphe...

~%

3,6-diphenylpyridazine Structure

3,6-diphenylpyr...

(5R,6R)-3,6-diphenyl-1,2-diazabicyclo[3.1.0]hex-2-ene Structure

(5R,6R)-3,6-dip...

~%

3,6-diphenylpyridazine Structure

3,6-diphenylpyr...

sodium salt of (E)-1,4-diphenyl-3-buten-1-one N-tosylhydrazone Structure

sodium salt of ...

~%

3,6-diphenylpyridazine Structure

3,6-diphenylpyr...

ethyl cyclopent-1-ene-1-acetate Structure

ethyl cyclopent...

~86%

2-(cyclopenten-1-yl)acetic acid Structure

2-(cyclopenten-...

ethyl 2-cyclopentylideneacetate Structure

ethyl 2-cyclope...

~%

2-(cyclopenten-1-yl)acetic acid Structure

2-(cyclopenten-...

Cyclopentanone Structure

~%

2-(cyclopenten-1-yl)acetic acid Structure

2-(cyclopenten-...

benzoylamino-phenyl-acetic acid 3-methyl-but-2-enyl ester Structure

benzoylamino-ph...

~%

4-methyl-1-phenylpent-3-en-1-one Structure

4-methyl-1-phen...

methyl 2-benzoylamino-2-phenyl-acetate Structure

methyl 2-benzoy...

~%

4-methyl-1-phenylpent-3-en-1-one Structure

4-methyl-1-phen...

sodium salt of 1-phenyl-4-penten-1-one N-tosylhydrazone Structure

sodium salt of ...

~%

4-Penten-1-one,1-phenyl- Structure

4-Penten-1-one,...

3,4-Dihydronaphthalen-1(2H)-one Structure

3,4-Dihydronaph...

~%

1,2,3,4-tetrahydronaphthalen-1-ylidine acetatic acid ethyl ester Structure

1,2,3,4-tetrahy...

1-Naphthaleneacetic acid, 1,2,3,4-tetrahydro-1-hydroxy-, ethyl ester Structure

1-Naphthaleneac...

~%

1,2,3,4-tetrahydronaphthalen-1-ylidine acetatic acid ethyl ester Structure

1,2,3,4-tetrahy...

ethyl 2-(3,4-dihydronaphthalen-1-yl)acetate Structure

ethyl 2-(3,4-di...

(4-chloro-benzoylamino)-phenyl-acetic acid 3-methyl-but-2-enyl ester Structure

(4-chloro-benzo...

~%

1-(4-chlorophenyl)-4-methylpent-3-en-1-one Structure

1-(4-chlorophen...

(4-chloro-benzoylamino)-phenyl-acetic acid methyl ester Structure

(4-chloro-benzo...

~%

1-(4-chlorophenyl)-4-methylpent-3-en-1-one Structure

1-(4-chlorophen...

Ethyl (1-hydroxycyclopentyl)acetate Structure

Ethyl (1-hydrox...

~0%

Ethyl 1-Cyclopentene-1-Carboxylate Structure

Ethyl 1-Cyclope...

ethyl 2-cyclopentylideneacetate Structure

ethyl 2-cyclope...

ethyl cyclopent-1-ene-1-acetate Structure

ethyl cyclopent...

1-Imidazolyl (alkyl)-substituted di-and tetrahydroquinolines...

[Jacobs, Christoph; Frotscher, Martin; Dannhardt, Gerd; Hartmann, Rolf W. Journal of Medicinal Chemistry, 2000 , vol. 43, # 9 p. 1841 - 1851]

An efficient entry into butenolides: Synthesis of (±) mintla...

[Chavan, Subhash P.; Zubaidha, P. K.; Ayyangar, Nagaraj R. Tetrahedron Letters, 1992 , vol. 33, # 32 p. 4605 - 4608]

Construction of functionalized indans by thallium (III) prom...

[Ferraz, Helena M.C; Silva Jr., Luiz F Tetrahedron, 2001 , vol. 57, # 50 p. 9939 - 9949]