Show the complete and detailed reaction mechanism (Curtius Rearrangement) of carboxylic acid 4 that resulted in the formation of isocyanate 5, which, upon electrocyclization furnished pyrrolo[2,3-c]quinoline 6. Intermediate 6 was subsequently transformed into triflate 7, and the total syntheses of marinoquinolines 3a, 3b, and 3e were accomplished by intro- ducing different substituents at the C4 position. (show movement of electrons, charges, arrows, reagents, conditions, biproducts etc. and provide short explanation)
Show the complete and detailed reaction mechanism (Curtius Rearrangement) of carboxylic acid 4 that resulted in the formation of isocyanate 5, which, upon electrocyclization furnished pyrrolo[2,3-c]quinoline 6. Intermediate 6 was subsequently transformed into triflate 7, and the total syntheses of marinoquinolines 3a, 3b, and 3e were accomplished by intro- ducing different substituents at the C4 position. (show movement of electrons, charges, arrows, reagents, conditions, biproducts etc. and provide short explanation)
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Question
Show the complete and detailed reaction mechanism (Curtius Rearrangement) of
![1)
EtzN
DPPA
NH
NH
1,2-DCB
60 °C, 30 min
CO2H
N=:=0
4
5
2)
NH
A
Tf20, Py
CH2CI2
rt, 30 min
120 °C, 30 min
'N'
NH
NH
'N'
OTf
R
3a: marinoquinoline A (R = Me)
3b: marinoquinoline B (R = iBu)
3e: marinoquinoline E (R = indol-3-yl)
7
introduction of tetrahydroquinoloine moiety by direct amination
NH
H
7
`N'
8a: X = CH2
8b: X = C=0](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F798b4bc7-99a9-4bb6-ad24-3facbe2fbb0e%2F999a3858-bce4-4706-b404-1b7ef8f1bf60%2Fj8sr0wm_processed.png&w=3840&q=75)
Transcribed Image Text:1)
EtzN
DPPA
NH
NH
1,2-DCB
60 °C, 30 min
CO2H
N=:=0
4
5
2)
NH
A
Tf20, Py
CH2CI2
rt, 30 min
120 °C, 30 min
'N'
NH
NH
'N'
OTf
R
3a: marinoquinoline A (R = Me)
3b: marinoquinoline B (R = iBu)
3e: marinoquinoline E (R = indol-3-yl)
7
introduction of tetrahydroquinoloine moiety by direct amination
NH
H
7
`N'
8a: X = CH2
8b: X = C=0
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