Answered: Show the complete and detailed reaction…

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter24: Amines And Heterocycles

Section24.SE: Something Extra

Problem 78AP

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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)

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

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

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