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An Unusual AlCl3 Catalysed Aromatic Cyclisation Reaction : Novel Synthesis of Tetrahydronaphthoic Acids†
TETRAHEDRON LETTERS TetrahedronLetters 39 (1998) 113-114
Pergamon
An Unusual AIC13Catalysed Aromatic Cyclisation Reaction : Novel Synthesis of TetrahydronaphthoicAcids+
Raghao S. Mali*, Milind D. Sindkhedkar and Prakash G, Jagtap GaswareResearchCentre,Departmentof Chemistry, Universityof Pune,Pune-411007, fNDIA (e-mail: rsmalifjchem.unipune.emet.in) Received 22 July 1997;revised 13October 1997;accepted24 October 1997 Abstract: An rmusuatAIC13catalysed aromatic cyclisationreactionis dcscribcd,This is used to developa novelsynthesisof 5,6,7,8-tetrahydro-5 -alkyl-l-naphthoicacids (la-d) from 2-vinylberrzoic acids(3a-d). O 1997Elsevier Science Ltd. All rights reserved.
Tetrahydro-1-naphthoic acids like lb and naphthoic acids (2a-b) are reported to possess uselirl biological activities132,Tetrahydronaphthoic acid (id) has been used as intermediatefor the synthesis of
naturallyoccurringpentacyclicphenanthrenehydrocarbons. The 5-methyl-l-naphthoicacids (2c and 2d) are also presentas structuralfeaturesin complex naturalproducts4likeazinomycinsA and B and neocarzinostatin
4’1
R2
a OH Me b H Me CH B d OH n-pr
3’1
‘2
a GMe Et bH f3 CH n-l% dH i-pr e OMe H fH H gH Me
1’1
R2 ,3
a OMeMe bH Me CH El dH Me
H H H Me
2,1
‘2
‘3 ‘4
aH H Me H bH H E H c H OMeMe H d OH H Me OMe
which are important antitumor antibiotics,In view of this various methods have been developedfor their synthesis3-5. In this paper we describean unusualAIC13catalysedaromaticcyclisationreactionwhichhas lead to a simplesynthesisof 5,6,7,8-tetrahydro-5-alkyl-l-naphthoicacids (la-d) Recentlydwe have developed a novel method for the synthesis of 3-methyl- and 3-ethy1(4a-c) fiorn 2-vinylbenzoicacids (3e-g) using aluminiumchloride,In this r~tion, 3,4-dihydroisocoumarins
0040-4039/98/$19.00 01997 Elsevier Science Ltd. All rights reserved. PIZ:S0040-4039(97)10462-2
114
2-vinylberrzoicacid underwenta lactonisationreactionby addition of the carboxylgroup across the double (4d) from 2-vinylbenzoic bond, In attemptingthe synthesisof 8-hydroxy-3-propyl-3,4-dihydroisocournarin
acid (E+Z, 3a), using aluminiumchloride in methylenechloride according to our procedure, surprisingly 5,6,7,8-tetrahydro-5 -methyl-l-naphthoic acid (la) was obtained in 65Y0 yield instead of the desired isocoumarim4d. The novelobservationof elkylation,insteadof lactonisatio~was rdsonoticedin the synthesis of 5,6,7,8-tetrahydro-5 -aUcyLl-naphthoicacids (Ibd)
from 2-vinylbenzoicacids7+b(3h-d), where the
l-naphthoicacids (lb-d) were obtainedin 62-727.yield. the The tetrahydro-5-alkyl-1-naphthoicacids (lb and IC) on aromatisationusing 10%Pal/Cfi.u-nished correspondingl-naphthoicacids (2a and 2b) in 62 and 66Y0yieldrespectively, Acknowledgement : MDS andPGJ thank CS~ New Delhifor the awardof seniorresearchfellowships. References and Notes:
t
Dedicatedto Prof.Dr.D. SSObach cmthecccasirmofhis60thbirth&y.
1
Thomscn,R. H. Naturally OccurringQuinones111:Recent Advances; Chapmanand Hall;Loodonand New York,1987.
2, (a) Fujita,T.; Koshirnizu,K.; Irnai,T.; Mitaui,T,; Kate, J. Agr. Biol. Chem. 1%1, 25, 710.(b) Fujita,T.; I. I.; Pshirkov,S. wa,T.; Kmhimizo,K,;Mitsui,T. Agr. Biol. Chem.1961,25,719.(c)Starovoitov, Komaza Yu,; Nefedova,M. Yu.; Yakovlev,G. L; Adanin,V. M.; Skryabin,G. K. Dokl.Akad.Nauk.SSSR1973,213, 1210,(Chem Abstn 8O:1O6843U, 1973).
3
Greioer,A. Ch.; Spyckerelle, C.;Albrecht,P. Tetrahedron1976,32,257.
4, (a) Shishido,K.; Omodani,T.; Shibuya, M. ./. Chem. Sm., Perkin Trans.Z 1992, 2053. (b) Meyers, A. G.; Subramaniam,V.;Harnrmmd,M. TetrahedronLett 1996,37,587. 5. (a) Wightman,R. H.; Laycack,D. E.; Avdovich,H. W. J Org. Chem.1978,43, 2167.(b) Meyers,A. L; Reuman,M.; G&l, R. A. J. Org Chem. 1981, 46, 783. (c) Tanis,S. P.; Abdallah,Y. M, Sjnth. Commun.
1986,16,251.(d) Parlow,J. Tetrahedron1994,50,3297. 6. Mali R. S.; Jagtap. P. G.; Patil,S. R.;Pawar,P.N. J Chem.%c., Chem.Commun.1992,883. 7. (a)MaliR. S.;Patil,S. R.; Kukarni, B. K.; Yeola, S. N. Id. J. Chem. 1990,29B, 319, (b) Mali,R. S.; Patil, S. R. Synth.Commun.1990,20,167. 8. TypicalProcedure: AnhydrousAIC1,(0.4g, 3 mmol)indry methykne chloride(5 ml) was stirred fir 15 min. and a solutionof 2-vinylbenzoicacid (34 0.220 g, 1 mmol)m metbylenechloride(5 ml) was addedto it. h was stirred at roomternpwature fbr lh, poured in ice cold HCI (1:1, 10 ml) and extracted with methykmechloride (2x 10 ml). The combinedorganic layer was washedwith water, dried (NazSOi)and evaporatedto give a solid over silica gel usrng ethyl acetaten-hexane (3:97) to afford naphthoic acid lq which was chronmtographed (0.143 g, 65%); m.p. 142-43”C;v_/cm-’ (nujol) 3200-2700, 1698; 6H(CDC13)1.27 (3H, d, J 7,6Hz, CHJ), 1.38-2.0(4H, m, -CHZCHZ-), 2.70-3.04 (3H, m, ArCHZ-,ArCH-), 3.86 (3H, s, OCH3),6.82 (lH, d, J 8.9 Hz, Ar-H), 7.26 (lH, d, J 8.9 Hz, A@.
Pergamon
An Unusual AIC13Catalysed Aromatic Cyclisation Reaction : Novel Synthesis of TetrahydronaphthoicAcids+
Raghao S. Mali*, Milind D. Sindkhedkar and Prakash G, Jagtap GaswareResearchCentre,Departmentof Chemistry, Universityof Pune,Pune-411007, fNDIA (e-mail: rsmalifjchem.unipune.emet.in) Received 22 July 1997;revised 13October 1997;accepted24 October 1997 Abstract: An rmusuatAIC13catalysed aromatic cyclisationreactionis dcscribcd,This is used to developa novelsynthesisof 5,6,7,8-tetrahydro-5 -alkyl-l-naphthoicacids (la-d) from 2-vinylberrzoic acids(3a-d). O 1997Elsevier Science Ltd. All rights reserved.
Tetrahydro-1-naphthoic acids like lb and naphthoic acids (2a-b) are reported to possess uselirl biological activities132,Tetrahydronaphthoic acid (id) has been used as intermediatefor the synthesis of
naturallyoccurringpentacyclicphenanthrenehydrocarbons. The 5-methyl-l-naphthoicacids (2c and 2d) are also presentas structuralfeaturesin complex naturalproducts4likeazinomycinsA and B and neocarzinostatin
4’1
R2
a OH Me b H Me CH B d OH n-pr
3’1
‘2
a GMe Et bH f3 CH n-l% dH i-pr e OMe H fH H gH Me
1’1
R2 ,3
a OMeMe bH Me CH El dH Me
H H H Me
2,1
‘2
‘3 ‘4
aH H Me H bH H E H c H OMeMe H d OH H Me OMe
which are important antitumor antibiotics,In view of this various methods have been developedfor their synthesis3-5. In this paper we describean unusualAIC13catalysedaromaticcyclisationreactionwhichhas lead to a simplesynthesisof 5,6,7,8-tetrahydro-5-alkyl-l-naphthoicacids (la-d) Recentlydwe have developed a novel method for the synthesis of 3-methyl- and 3-ethy1(4a-c) fiorn 2-vinylbenzoicacids (3e-g) using aluminiumchloride,In this r~tion, 3,4-dihydroisocoumarins
0040-4039/98/$19.00 01997 Elsevier Science Ltd. All rights reserved. PIZ:S0040-4039(97)10462-2
114
2-vinylberrzoicacid underwenta lactonisationreactionby addition of the carboxylgroup across the double (4d) from 2-vinylbenzoic bond, In attemptingthe synthesisof 8-hydroxy-3-propyl-3,4-dihydroisocournarin
acid (E+Z, 3a), using aluminiumchloride in methylenechloride according to our procedure, surprisingly 5,6,7,8-tetrahydro-5 -methyl-l-naphthoic acid (la) was obtained in 65Y0 yield instead of the desired isocoumarim4d. The novelobservationof elkylation,insteadof lactonisatio~was rdsonoticedin the synthesis of 5,6,7,8-tetrahydro-5 -aUcyLl-naphthoicacids (Ibd)
from 2-vinylbenzoicacids7+b(3h-d), where the
l-naphthoicacids (lb-d) were obtainedin 62-727.yield. the The tetrahydro-5-alkyl-1-naphthoicacids (lb and IC) on aromatisationusing 10%Pal/Cfi.u-nished correspondingl-naphthoicacids (2a and 2b) in 62 and 66Y0yieldrespectively, Acknowledgement : MDS andPGJ thank CS~ New Delhifor the awardof seniorresearchfellowships. References and Notes:
t
Dedicatedto Prof.Dr.D. SSObach cmthecccasirmofhis60thbirth&y.
1
Thomscn,R. H. Naturally OccurringQuinones111:Recent Advances; Chapmanand Hall;Loodonand New York,1987.
2, (a) Fujita,T.; Koshirnizu,K.; Irnai,T.; Mitaui,T,; Kate, J. Agr. Biol. Chem. 1%1, 25, 710.(b) Fujita,T.; I. I.; Pshirkov,S. wa,T.; Kmhimizo,K,;Mitsui,T. Agr. Biol. Chem.1961,25,719.(c)Starovoitov, Komaza Yu,; Nefedova,M. Yu.; Yakovlev,G. L; Adanin,V. M.; Skryabin,G. K. Dokl.Akad.Nauk.SSSR1973,213, 1210,(Chem Abstn 8O:1O6843U, 1973).
3
Greioer,A. Ch.; Spyckerelle, C.;Albrecht,P. Tetrahedron1976,32,257.
4, (a) Shishido,K.; Omodani,T.; Shibuya, M. ./. Chem. Sm., Perkin Trans.Z 1992, 2053. (b) Meyers, A. G.; Subramaniam,V.;Harnrmmd,M. TetrahedronLett 1996,37,587. 5. (a) Wightman,R. H.; Laycack,D. E.; Avdovich,H. W. J Org. Chem.1978,43, 2167.(b) Meyers,A. L; Reuman,M.; G&l, R. A. J. Org Chem. 1981, 46, 783. (c) Tanis,S. P.; Abdallah,Y. M, Sjnth. Commun.
1986,16,251.(d) Parlow,J. Tetrahedron1994,50,3297. 6. Mali R. S.; Jagtap. P. G.; Patil,S. R.;Pawar,P.N. J Chem.%c., Chem.Commun.1992,883. 7. (a)MaliR. S.;Patil,S. R.; Kukarni, B. K.; Yeola, S. N. Id. J. Chem. 1990,29B, 319, (b) Mali,R. S.; Patil, S. R. Synth.Commun.1990,20,167. 8. TypicalProcedure: AnhydrousAIC1,(0.4g, 3 mmol)indry methykne chloride(5 ml) was stirred fir 15 min. and a solutionof 2-vinylbenzoicacid (34 0.220 g, 1 mmol)m metbylenechloride(5 ml) was addedto it. h was stirred at roomternpwature fbr lh, poured in ice cold HCI (1:1, 10 ml) and extracted with methykmechloride (2x 10 ml). The combinedorganic layer was washedwith water, dried (NazSOi)and evaporatedto give a solid over silica gel usrng ethyl acetaten-hexane (3:97) to afford naphthoic acid lq which was chronmtographed (0.143 g, 65%); m.p. 142-43”C;v_/cm-’ (nujol) 3200-2700, 1698; 6H(CDC13)1.27 (3H, d, J 7,6Hz, CHJ), 1.38-2.0(4H, m, -CHZCHZ-), 2.70-3.04 (3H, m, ArCHZ-,ArCH-), 3.86 (3H, s, OCH3),6.82 (lH, d, J 8.9 Hz, Ar-H), 7.26 (lH, d, J 8.9 Hz, A@.