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

The Journal of Organic Chemistry

Intramolecular reactions of azidoalkenes. The 2-(azidoalkyl) quinone rearrangement

AG Schultz, WG McMahon

Index: Schultz, Arthur G.; McMahon, Wayne G. Journal of Organic Chemistry, 1984 , vol. 49, # 9 p. 1676 - 1678

Full Text: HTML

Citation Number: 21

Abstract

Summary: Rearrangements of 2-(azidopropyl)-l, 4-benzo-and-1, 4-naphthoquinones give 2- (2-A1-pyrro1inyl)-4-cyclopentene-1, 3-diones and pyrrolidino [2, 1-b] azepine-1, 5-diones via intermediate triazolines. Acid-catalyzed triazoline isomerization to an isolable diazo enedione is reported.

1,2,5-trimethyl-3-phenylmethoxy-4-prop-2-enylbenzene Structure

1,2,5-trimethyl...

~%

2-(3-azidopropyl)-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione Structure

2-(3-azidopropy...

O-benzyl-eugenol Structure

O-benzyl-eugenol

~%

2-(3-azidopropyl)-6-methoxycyclohexa-2,5-diene-1,4-dione Structure

2-(3-azidopropy...

2,4,5-trimethyl-2-(2-Δ1-pyrrolinyl)-4-cyclopentene-1,3-dione Structure

2,4,5-trimethyl...

~49%

6,7,9-trimethyl-2,3-dihydro-1H-pyrrolo[1,2-a]azepine-5,8-dione Structure

6,7,9-trimethyl...

2-(3-azidopropyl)-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione Structure

2-(3-azidopropy...

~%

2,4,5-trimethyl-2-(2-Δ1-pyrrolinyl)-4-cyclopentene-1,3-dione Structure

2,4,5-trimethyl...

6,7,9-trimethyl-2,3-dihydro-1H-pyrrolo[1,2-a]azepine-5,8-dione Structure

6,7,9-trimethyl...

2-allyl-1,4-dimethoxy-3-methylnaphthalene Structure

2-allyl-1,4-dim...

~%

2-METHYL-1,3-INDANDIONE Structure

2-METHYL-1,3-IN...

2-(3-azidopropyl)-3-methylnaphthalene-1,4-dione Structure

2-(3-azidopropy...

~%

2-METHYL-1,3-INDANDIONE Structure

2-METHYL-1,3-IN...

2-(3,4-dihydro-2H-pyrrol-5-yl)-2-methylindene-1,3-dione Structure

2-(3,4-dihydro-...

~%

2-METHYL-1,3-INDANDIONE Structure

2-METHYL-1,3-IN...

2-(3-azidopropyl)-6-methoxycyclohexa-2,5-diene-1,4-dione Structure

2-(3-azidopropy...

~%

10-diazonio-7-methoxy-6-oxo-1-azaspiro[4.5]deca-7,9-dien-9-olate Structure

10-diazonio-7-m...

(6aS,10aR)-9-methoxy-2,3-dihydro-1H,10H-benzo[d]pyrrolo[1,2-c][1,2,3]triazole-7,10(6aH)-dione Structure

(6aS,10aR)-9-me...

4-methoxy-2-pyrrolidin-2-ylidenecyclopent-4-ene-1,3-dione Structure

4-methoxy-2-pyr...

Detail

(6aS,10aR)-9-methoxy-2,3-dihydro-1H,10H-benzo[d]pyrrolo[1,2-c][1,2,3]triazole-7,10(6aH)-dione Structure

(6aS,10aR)-9-me...

~%

10-diazonio-7-methoxy-6-oxo-1-azaspiro[4.5]deca-7,9-dien-9-olate Structure

10-diazonio-7-m...

2-(3-azidopropyl)-6-methoxycyclohexa-2,5-diene-1,4-dione Structure

2-(3-azidopropy...

~0%

N/A Structure

10-diazonio-7-methoxy-6-oxo-1-azaspiro[4.5]deca-7,9-dien-9-olate Structure

10-diazonio-7-m...

(6aS,10aR)-9-methoxy-2,3-dihydro-1H,10H-benzo[d]pyrrolo[1,2-c][1,2,3]triazole-7,10(6aH)-dione Structure

(6aS,10aR)-9-me...

Detail

(6aS,10aR)-9-methoxy-2,3-dihydro-1H,10H-benzo[d]pyrrolo[1,2-c][1,2,3]triazole-7,10(6aH)-dione Structure

(6aS,10aR)-9-me...

~%

4-methoxy-2-pyrrolidin-2-ylidenecyclopent-4-ene-1,3-dione Structure

4-methoxy-2-pyr...

2-(3-azidopropyl)-6-methoxycyclohexa-2,5-diene-1,4-dione Structure

2-(3-azidopropy...

~%

N/A Structure

(6aS,10aR)-9-methoxy-2,3-dihydro-1H,10H-benzo[d]pyrrolo[1,2-c][1,2,3]triazole-7,10(6aH)-dione Structure

(6aS,10aR)-9-me...

4-methoxy-2-pyrrolidin-2-ylidenecyclopent-4-ene-1,3-dione Structure

4-methoxy-2-pyr...

Detail

2-(3-azidopropyl)-6-methoxycyclohexa-2,5-diene-1,4-dione Structure

2-(3-azidopropy...

~%

10-diazonio-7-methoxy-6-oxo-1-azaspiro[4.5]deca-7,9-dien-9-olate Structure

10-diazonio-7-m...

(6aS,10aR)-9-methoxy-2,3-dihydro-1H,10H-benzo[d]pyrrolo[1,2-c][1,2,3]triazole-7,10(6aH)-dione Structure

(6aS,10aR)-9-me...

4-methoxy-2-pyrrolidin-2-ylidenecyclopent-4-ene-1,3-dione Structure

4-methoxy-2-pyr...

Detail

10-diazonio-7-methoxy-6-oxo-1-azaspiro[4.5]deca-7,9-dien-9-olate Structure

10-diazonio-7-m...

~%

4-methoxy-2-pyrrolidin-2-ylidenecyclopent-4-ene-1,3-dione Structure

4-methoxy-2-pyr...

N/A Structure

2-(3-azidopropyl)-6-methoxycyclohexa-2,5-diene-1,4-dione Structure

2-(3-azidopropy...

~0%

N/A Structure

10-diazonio-7-methoxy-6-oxo-1-azaspiro[4.5]deca-7,9-dien-9-olate Structure

10-diazonio-7-m...

(6aS,10aR)-9-methoxy-2,3-dihydro-1H,10H-benzo[d]pyrrolo[1,2-c][1,2,3]triazole-7,10(6aH)-dione Structure

(6aS,10aR)-9-me...

Detail

2-allyl-1,4-dimethoxy-3-methylnaphthalene Structure

2-allyl-1,4-dim...

~%

2-(3-azidopropyl)-3-methylnaphthalene-1,4-dione Structure

2-(3-azidopropy...

2-allyl-1,4-dimethoxy-3-methylnaphthalene Structure

2-allyl-1,4-dim...

~%

2-(3,4-dihydro-2H-pyrrol-5-yl)-2-methylindene-1,3-dione Structure

2-(3,4-dihydro-...

2-(3-azidopropyl)-3-methylnaphthalene-1,4-dione Structure

2-(3-azidopropy...

~%

2-(3,4-dihydro-2H-pyrrol-5-yl)-2-methylindene-1,3-dione Structure

2-(3,4-dihydro-...

N/A Structure