Functionalised benzocyclo-octenones

Synthesis and chemistry

Ahmed Chenna, John Donnelly, Kevin J. McCullough, George R. Proctor, James Redpath

Research output: Contribution to journalArticle

Abstract

10,11-Dihydro-5-hydroxy-4-methoxycarbonylbenzo[5,6]cyclo-octa[1,2-c] furan-1,3-dione was selectively reduced and hydrolysed to 4,5-dihydrobenzo[5,6] cyclo-octa[1,2-c]furan-1,10(3H,11H)-dione whose structure was confirmed by X-ray analysis. Reduction and dehydration gave the lactone 10,11-dihydrobenzo[5,6] cyclo-octa[1,2-c]furan-1(3H)-one which was identical with one of two isomers obtained when the anhydride 10,11-dihydrobenzo[5,6]cyclo-octa[1,2-c]furan-1,3, 5(4H)-trione was reduced and dehydrated. Products of bromination of 10,11-dihydrobenzo[5,6]cyclo-octa[1,2-c]furan-1,3,5(4H)-trione and its methyl enol ether were identified: the enol ether was converted into several imides which could not be cleanly reduced. 4,5-Dihydrobenzo[5,6]cyclo-octa[1,2-c]furan- 1,10(3H,11H)-dione was converted into the following lactones: 4,5,10,11-tetrahydro-10-hydroxybenzo[5,6]cyclo-octa[1,2-c]furan-1 (3H)-one; 4,5-dihydrobenzo[5,6]cyclo-octa[1,2-c]furan-1(3H/)-one; 3a,4,5,10,11,11a- hexahydro-10-hydroxybenzo[5,6]cyclo-octa[1,2-c]furan-1(3H)-one; 4,5,10,11-tetrahydro-10-hydroxybenzo[5,6]cyclo-octa[1,2-c]furan-1 (3H)-one; 3a,4,5,11a-tetrahydrobenzo[5,6]cyclo-octa[1,2-c]furan-1,10(3H,11H)dione; 3a,4,5,11a-tetrahydrobenzo[5,6]cyclo-octa[1,2-c]furan-1(3H)-one. Reaction of appropriate lactones with benzylamine and benzylamine hydrochloride or with methylamine and hydrogen chloride gave lactams which were reduced to N-benzyl or N-methyl benzo[5,6]cyclo-octa[1,2-c]pyrrole derivatives. N-Benzyl analogues were debenzylated via carbamates. 4,5,10,11-Tetrahydro-10-hy7droxybenzo[5,6] cyclo-octa[1,2-c]furan-1(3H)-one was arylated with anisole in the presence of acid to yield 4,5,10,11-tetrahydro-p-methoxyphenylbenzo[5,6]cyclo-octa[1,2-c] furan-1 (3H)-one.

Original languageEnglish
Pages (from-to)261-270
Number of pages10
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number2
Publication statusPublished - 1990

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Lactones
furan
Ether
Imides
Lactams
Pyrroles
Carbamates
Hydrochloric Acid
Anhydrides
X ray analysis
Dehydration
Isomers
Derivatives
Acids
benzylamine

Cite this

Chenna, A., Donnelly, J., McCullough, K. J., Proctor, G. R., & Redpath, J. (1990). Functionalised benzocyclo-octenones: Synthesis and chemistry. Journal of the Chemical Society, Perkin Transactions 1, (2), 261-270.
Chenna, Ahmed ; Donnelly, John ; McCullough, Kevin J. ; Proctor, George R. ; Redpath, James. / Functionalised benzocyclo-octenones : Synthesis and chemistry. In: Journal of the Chemical Society, Perkin Transactions 1. 1990 ; No. 2. pp. 261-270.
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abstract = "10,11-Dihydro-5-hydroxy-4-methoxycarbonylbenzo[5,6]cyclo-octa[1,2-c] furan-1,3-dione was selectively reduced and hydrolysed to 4,5-dihydrobenzo[5,6] cyclo-octa[1,2-c]furan-1,10(3H,11H)-dione whose structure was confirmed by X-ray analysis. Reduction and dehydration gave the lactone 10,11-dihydrobenzo[5,6] cyclo-octa[1,2-c]furan-1(3H)-one which was identical with one of two isomers obtained when the anhydride 10,11-dihydrobenzo[5,6]cyclo-octa[1,2-c]furan-1,3, 5(4H)-trione was reduced and dehydrated. Products of bromination of 10,11-dihydrobenzo[5,6]cyclo-octa[1,2-c]furan-1,3,5(4H)-trione and its methyl enol ether were identified: the enol ether was converted into several imides which could not be cleanly reduced. 4,5-Dihydrobenzo[5,6]cyclo-octa[1,2-c]furan- 1,10(3H,11H)-dione was converted into the following lactones: 4,5,10,11-tetrahydro-10-hydroxybenzo[5,6]cyclo-octa[1,2-c]furan-1 (3H)-one; 4,5-dihydrobenzo[5,6]cyclo-octa[1,2-c]furan-1(3H/)-one; 3a,4,5,10,11,11a- hexahydro-10-hydroxybenzo[5,6]cyclo-octa[1,2-c]furan-1(3H)-one; 4,5,10,11-tetrahydro-10-hydroxybenzo[5,6]cyclo-octa[1,2-c]furan-1 (3H)-one; 3a,4,5,11a-tetrahydrobenzo[5,6]cyclo-octa[1,2-c]furan-1,10(3H,11H)dione; 3a,4,5,11a-tetrahydrobenzo[5,6]cyclo-octa[1,2-c]furan-1(3H)-one. Reaction of appropriate lactones with benzylamine and benzylamine hydrochloride or with methylamine and hydrogen chloride gave lactams which were reduced to N-benzyl or N-methyl benzo[5,6]cyclo-octa[1,2-c]pyrrole derivatives. N-Benzyl analogues were debenzylated via carbamates. 4,5,10,11-Tetrahydro-10-hy7droxybenzo[5,6] cyclo-octa[1,2-c]furan-1(3H)-one was arylated with anisole in the presence of acid to yield 4,5,10,11-tetrahydro-p-methoxyphenylbenzo[5,6]cyclo-octa[1,2-c] furan-1 (3H)-one.",
author = "Ahmed Chenna and John Donnelly and McCullough, {Kevin J.} and Proctor, {George R.} and James Redpath",
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Chenna, A, Donnelly, J, McCullough, KJ, Proctor, GR & Redpath, J 1990, 'Functionalised benzocyclo-octenones: Synthesis and chemistry', Journal of the Chemical Society, Perkin Transactions 1, no. 2, pp. 261-270.

Functionalised benzocyclo-octenones : Synthesis and chemistry. / Chenna, Ahmed; Donnelly, John; McCullough, Kevin J.; Proctor, George R.; Redpath, James.

In: Journal of the Chemical Society, Perkin Transactions 1, No. 2, 1990, p. 261-270.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Functionalised benzocyclo-octenones

T2 - Synthesis and chemistry

AU - Chenna, Ahmed

AU - Donnelly, John

AU - McCullough, Kevin J.

AU - Proctor, George R.

AU - Redpath, James

PY - 1990

Y1 - 1990

N2 - 10,11-Dihydro-5-hydroxy-4-methoxycarbonylbenzo[5,6]cyclo-octa[1,2-c] furan-1,3-dione was selectively reduced and hydrolysed to 4,5-dihydrobenzo[5,6] cyclo-octa[1,2-c]furan-1,10(3H,11H)-dione whose structure was confirmed by X-ray analysis. Reduction and dehydration gave the lactone 10,11-dihydrobenzo[5,6] cyclo-octa[1,2-c]furan-1(3H)-one which was identical with one of two isomers obtained when the anhydride 10,11-dihydrobenzo[5,6]cyclo-octa[1,2-c]furan-1,3, 5(4H)-trione was reduced and dehydrated. Products of bromination of 10,11-dihydrobenzo[5,6]cyclo-octa[1,2-c]furan-1,3,5(4H)-trione and its methyl enol ether were identified: the enol ether was converted into several imides which could not be cleanly reduced. 4,5-Dihydrobenzo[5,6]cyclo-octa[1,2-c]furan- 1,10(3H,11H)-dione was converted into the following lactones: 4,5,10,11-tetrahydro-10-hydroxybenzo[5,6]cyclo-octa[1,2-c]furan-1 (3H)-one; 4,5-dihydrobenzo[5,6]cyclo-octa[1,2-c]furan-1(3H/)-one; 3a,4,5,10,11,11a- hexahydro-10-hydroxybenzo[5,6]cyclo-octa[1,2-c]furan-1(3H)-one; 4,5,10,11-tetrahydro-10-hydroxybenzo[5,6]cyclo-octa[1,2-c]furan-1 (3H)-one; 3a,4,5,11a-tetrahydrobenzo[5,6]cyclo-octa[1,2-c]furan-1,10(3H,11H)dione; 3a,4,5,11a-tetrahydrobenzo[5,6]cyclo-octa[1,2-c]furan-1(3H)-one. Reaction of appropriate lactones with benzylamine and benzylamine hydrochloride or with methylamine and hydrogen chloride gave lactams which were reduced to N-benzyl or N-methyl benzo[5,6]cyclo-octa[1,2-c]pyrrole derivatives. N-Benzyl analogues were debenzylated via carbamates. 4,5,10,11-Tetrahydro-10-hy7droxybenzo[5,6] cyclo-octa[1,2-c]furan-1(3H)-one was arylated with anisole in the presence of acid to yield 4,5,10,11-tetrahydro-p-methoxyphenylbenzo[5,6]cyclo-octa[1,2-c] furan-1 (3H)-one.

AB - 10,11-Dihydro-5-hydroxy-4-methoxycarbonylbenzo[5,6]cyclo-octa[1,2-c] furan-1,3-dione was selectively reduced and hydrolysed to 4,5-dihydrobenzo[5,6] cyclo-octa[1,2-c]furan-1,10(3H,11H)-dione whose structure was confirmed by X-ray analysis. Reduction and dehydration gave the lactone 10,11-dihydrobenzo[5,6] cyclo-octa[1,2-c]furan-1(3H)-one which was identical with one of two isomers obtained when the anhydride 10,11-dihydrobenzo[5,6]cyclo-octa[1,2-c]furan-1,3, 5(4H)-trione was reduced and dehydrated. Products of bromination of 10,11-dihydrobenzo[5,6]cyclo-octa[1,2-c]furan-1,3,5(4H)-trione and its methyl enol ether were identified: the enol ether was converted into several imides which could not be cleanly reduced. 4,5-Dihydrobenzo[5,6]cyclo-octa[1,2-c]furan- 1,10(3H,11H)-dione was converted into the following lactones: 4,5,10,11-tetrahydro-10-hydroxybenzo[5,6]cyclo-octa[1,2-c]furan-1 (3H)-one; 4,5-dihydrobenzo[5,6]cyclo-octa[1,2-c]furan-1(3H/)-one; 3a,4,5,10,11,11a- hexahydro-10-hydroxybenzo[5,6]cyclo-octa[1,2-c]furan-1(3H)-one; 4,5,10,11-tetrahydro-10-hydroxybenzo[5,6]cyclo-octa[1,2-c]furan-1 (3H)-one; 3a,4,5,11a-tetrahydrobenzo[5,6]cyclo-octa[1,2-c]furan-1,10(3H,11H)dione; 3a,4,5,11a-tetrahydrobenzo[5,6]cyclo-octa[1,2-c]furan-1(3H)-one. Reaction of appropriate lactones with benzylamine and benzylamine hydrochloride or with methylamine and hydrogen chloride gave lactams which were reduced to N-benzyl or N-methyl benzo[5,6]cyclo-octa[1,2-c]pyrrole derivatives. N-Benzyl analogues were debenzylated via carbamates. 4,5,10,11-Tetrahydro-10-hy7droxybenzo[5,6] cyclo-octa[1,2-c]furan-1(3H)-one was arylated with anisole in the presence of acid to yield 4,5,10,11-tetrahydro-p-methoxyphenylbenzo[5,6]cyclo-octa[1,2-c] furan-1 (3H)-one.

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Chenna A, Donnelly J, McCullough KJ, Proctor GR, Redpath J. Functionalised benzocyclo-octenones: Synthesis and chemistry. Journal of the Chemical Society, Perkin Transactions 1. 1990;(2):261-270.