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Microwave Assisted Intramolecular Dehydrogenative Dehydro-Diels Alder Approach to Substituted Benzofused Heterocycles

Proto, Justin (2016) Microwave Assisted Intramolecular Dehydrogenative Dehydro-Diels Alder Approach to Substituted Benzofused Heterocycles. Master's Thesis, University of Pittsburgh. (Unpublished)

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The emergence of benzo[b]thiophenes and benzo[b]furans as biologically useful scaffolds is of growing attention in medicine as natural products and pharmaceutical drugs. The means to produce these synthetic cores quickly and from economic starting materials has garnered much attention. Much of the current methodology is focused on formation of the heterocyclic ring annulation from benzene derivatives. However, the mechanistic restraints ofthis chemistry narrows the substitutional scope of the resulting benzo-fused heterocycles. Presented here is a simple methodology to produce uniquely substituted benzo[b]thiophenes and benzo[b]furans via the intramolecular dehydro-Diels-Alder reaction induced by microwave heating. Starting from aromatic heterocycles and focusing on a strategy of benzene annulation from heterocyclic-diene alkynyl-dienophile pairs forming tricyclic fused heterocycles were readily synthesized. The allowance of major product selection was demonstrated by solvent choice during heating; fully aromatic heterocycles were favored when PhNO2 was chosen, in as little as 10% by volume. The use of DMF favored the formation of dihydroheterocycles. The reaction showed a tolerance of terminal alkyne substitution and generally produced good yields.


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Item Type: University of Pittsburgh ETD
Status: Unpublished
CreatorsEmailPitt UsernameORCID
Proto, Justinjtp40@pitt.eduJTP40
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairBrummond, Kaykbrummon@pitt.eduKBRUMMON
Committee MemberHorne, Sethhorne@pitt.eduHORNE
Committee MemberFloreancig, Paulflorean@pitt.eduFLOREAN
Date: 20 September 2016
Date Type: Publication
Defense Date: 14 April 2016
Approval Date: 20 September 2016
Submission Date: 8 July 2016
Access Restriction: No restriction; Release the ETD for access worldwide immediately.
Number of Pages: 204
Institution: University of Pittsburgh
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Degree: MS - Master of Science
Thesis Type: Master's Thesis
Refereed: Yes
Uncontrolled Keywords: Benzofused Heterocycles, Diels Alder, intramolecular, microwave assisted
Date Deposited: 20 Sep 2016 20:32
Last Modified: 15 Nov 2016 14:34


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