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Vanida Bhavakul. Synthetic utilities of the enamides for the synthesis of some alkaloids. Doctoral Degree(Organic Chemistry). Mahidol University. Mahidol University Library and Knowledge Center. : Mahidol University, 1990.
Synthetic utilities of the enamides for the synthesis of some alkaloids
การนำสารอีนาไมด์มาใช้ประโยชน์ในการสังเคราะห์อัลคาลอยด์
Name: Vanida Bhavakul
LCSH:
Alkaloids
-- Biosynthesis
LCSH:
Enamides
LCSH:
Latex, Synthetic
Abstract:
Chapter I The reaction of various enamide derivatives with thallium (III) nitrate was investigated. Three different pathways were found to involve in such a reaction depaending on the structural feature of the enamide intermediates. In the case of enamides derived from N-acylation of the simple l-alkyl-3,4-dihydroisoquinolines, the rearrangement of the isoquinoline nucleus to the benzazepine derivative was observed. This finding of the crucial ring enlargement made the synthesis of the useful benzazepine derivatives more accessible. However, in the case of the enamides derived from the more complex l-benzyl and l-substituted benzyl-3,4- dihydroisoquinolines and the nitrogen atom substitured with alkoxycarbonyl groups or phenoxycarbonyl grous, the corresponding oxazolidone derivatives were the products of the reaction. The synthetic utility of the derived oxazolidone was briefly investigated. Moreover, in the third type of enamides dervied from l-benzyl and l-substituted benzyl-3,4-dihydroisquinoline with the nitrogen atom substituted with aroyl groups, the oxazolines were obtained. The mechanistic details of the above reactions were also discussed. Thermal rearrangement of various enamides was also invertigated. It was found that 1,3-acyl shift from the nitrogen atom to the carbon atom to give the vinylogous amide was observed upon heating of the enamide intermediates. The above finding proved that the thermal of the enamide is a viable process in contrast with the previously accepted view. Three approaches for the synthesis of isoindoloisoquinoline alkaloids were developed. The analysis of the syntheses of these alkaloids in term of bond formation was discussed. In the first approach, carbon-carbon bond formation ortho tothe side chain was effected followed by carbon-nitrogen bondformation. Final electrophilic aromatic substitutioncompleted the final carbon-carbon bond formation. In thesecond approach, the (aromatic) carbon-carbon bond was formedfirst which was then followed by the formation of carbon-carbonbond and carbonnitrogen bond respectively. Moreover, in the thirdapproach the isoquinoline ring was formed first, however unlikethe first two approaches, the formation of the isoquinoline ringis intermolecular reaction rather than the intramolecularreaction, the reaction was completed by the intramolecular lactambond formation.
Mahidol University. Mahidol University Library and Knowledge Center
Address:
NAKHONPATHOM
Email:
liwww@mahidol.ac.th
Name: Somsak Ruchirawat
Role:
Thesis Advisors
Name: Yodhathai Thebtaranonth
Role:
Thesis Advisors
Name: Sunanta Vibuljan
Role:
Thesis Advisors
Created:
1990
Modified:
2018-03-09
Issued:
2018-03-09
วิทยานิพนธ์/Thesis
application/pdf
eng
DegreeName: Doctor of Philosophy
Level: Doctoral Degree
Descipline: Organic Chemistry
Grantor: Mahidol University
©copyrights Mahidol University
RightsAccess:
ใช้เวลา
-0.581408 วินาที
Vanida Bhavakul
| Title | Contributor | Type |
|---|---|---|
| การวิเคราะห์ปริมาณตะกั่วในสิ่งตีพิมพ์โดยวิสิเบิลสเปคโตรโฟโตมิเตอร์
มหาวิทยาลัยเทคโนโลยีพระจอมเกล้าธนบุรี สุรศักดิ์ สุจริตวณิชพงศ์;วนิดา พวกุล;Surasak Sujaritvanichpong;Vanida Bhavakul | บทความ/Article | |
| Synthetic utilities of the enamides for the synthesis of some alkaloids
มหาวิทยาลัยมหิดล Vanida Bhavakul | Somsak Ruchirawat Yodhathai Thebtaranonth Sunanta Vibuljan | วิทยานิพนธ์/Thesis |
Somsak Ruchirawat
Yodhathai Thebtaranonth
Sunanta Vibuljan