Toward understanding the scope of Baylis-Hillman reaction: Synthesis of 3-(2- hydroxyphenyl)indolin-2-ones and polycyclic fused furans

Tetrahedron

Volumn 66, Issue 30, 2010, Pages 5612-5622

  Basavaiah, Deevi ^a   Roy, Suparna ^a   Das, Utpal ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

2 diones; 3 (2 Hydroxyphenyl)indolin 2 ones; Baylis Hillman reaction; Cyclic 1; Cycloalk 2 enones; Polycyclic fused furans

Indexed keywords

1 BENZYL 3 (2 HYDROXYPHENYL) 1 METHYLINDOLIN 2 ONE; 1 BENZYL 5 BROMO 3 (2 HYDROXYPHENYL) 1 METHYLINDOLIN 2 ONE; 1 BENZYL 5 CHLORO3 (2 HYDROXYPHENYL) 1 METHYLINDOLIN 2 ONE; 1 BENZYLE 3 (2 HYDROXYPHENYL) 1 METHYLINDOLIN 2 ONE; 1 ETHYL 3 (2 HYDROXYPHENYL) 1 METHYLINDOLIN 2 ONE; 2 OXAHEXACYCLO[15.3.0.0. 3,16 1. 4,8 2. 4(8),11 2. 4(8),15]DOCOSANE 1 (17),3(16),4(21),5,7,9,11,13,15(22) NONAEN 18 ONE; 2 OXAHEXACYCLO[15.4.0.0. 3,16 1.4,8 2. 4(8),112. 4(8),15]TRICOSANE 1 (17),3(16),4(22),5,7,9,11,13,15(23) NONAEN 18 ONE; 2 OXAPENTACYCLO [15.4.0.0. 3,16 0. 4,9 0. 10,15]HENICOSAN 1(17),3(16), 4(9),5,7,10(15),11,13 OCTAEN 18 ONE; 2 OXAPENTACYCLO[15.3.0.0. 3,16 0. 4,9 0. 10,15]COSAN 1(17), 3(16),4(9),5,7,10(15),11,13 OCTAEN 18 ONE; 20,20 DIMETHYL 2 OXAHEXACYCLO[15.4.0.0. 3,16 1. 4,8 2. 4(8),11 2. 4(8),15]TRICOSANE-1(17),3(16),4(22),5,7,9,11,13,15(23) NONAEN 18 ONE; 20,20 DIMETHYL 2 OXAPENTACYCLO[15.4.0.0.3 ,16 0. 4,9 0. 10,15]HENICOSAN 1(17),3(16),4(9),5,7,10(15),11,13 OCTAEN 18 ONE; 3 (2 HYDROXYPHENYL) 1 METHYLINDOLIN 2 ONE; 3 (2 HYDROXYPHENYL) 1 PHENYLINDOLIN 2 ONE; 3 (2 HYDROXYPHENYL) 5 METHYL 1 PHENYLINDOLIN 2 ONE; 5 CHLORO 1 ETHYL 3 (2 HYDROXYPHENYL) 1 METHYLINDOLIN 2 ONE; 5 CHLORO 3 (2 HYDROXYPHENYL) 1 METHYLINDOLIN 2 ONE; 5 CHLORO 3 (2 HYDROXYPHENYL) 1 PHENYLINDOLIN 2 ONE; ALCOHOL; CYCLOHEXENE DERIVATIVE; FURAN DERIVATIVE; INDOLE DERIVATIVE; ISATIN DERIVATIVE; TITANIUM TETRACHLORIDE; UNCLASSIFIED DRUG;

ARTICLE; BAYLIS HILLMAN REACTION; DRUG STRUCTURE; ONE POT SYNTHESIS; PRIORITY JOURNAL; SUBSTITUTION REACTION;

EID: 77955927309     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.05.087     Document Type: Article

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71. Detailed X-ray crystallographic data is available from the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK. CCDC numbers for compounds 4b, 4c, 4g, 20, 21, 23, and 27 are 753, 488, 753, 489, 753, 490, 753, 491, 754, 879, 754, 880, and 754, 881, respectively.
72. The TiCl4-mediated B-H reaction between aromatic 1, 2-diones [(9, 10)-phe- nanthrenedione and pyrene-(4, 5)-dione] and alkyl vinyl ketones at room temperature (35-37°C) (summer time room temperature in Hyderabad) provided fused furan derivatives. Ref: Basavaiah, D.; Sreenivasulu, B.; Rao, J. S. Tetrahedron Lett. 2001, 42, 1147-1149.
73. During the present study, we noticed that the TiCl4-mediated B-H reaction of [9, 10]-phenanthrenedione with MVK at 25-28°C (winter time room temperature in Hyderabad) for 3 h provided the fused furan derivatives (40%) along with the corresponding B-H alcohols (30%). At 35°C we obtained the fused furan derivative in 68% isolated yield.
74. cis-cis-cis-Stereochemistry is assigned to the compounds 27 and 28 as they contain C-C bonds (C3-C4, C12-C21, C1'-C2'), connecting acenaphthene rings, on the same side. Compounds 27 and 28 are racemic [1:1 mixture of compounds with 3R, 20(1')R, 21S, and 3S, 20(1')S, 21R stereochemistry] and only one form is shown in the structures.
75. Single crystal of 27 contains one disordered CH2Cl2 molecule.
76. 13C NMR spectrum of the compound 27 in CDCl3 showed 34 signals in which two signals, at d 123.86 and d 127.14, were more intense (long peaks) indicating that each of these signals arose due to two carbons (total four carbons). Thus total number of signals (36) and total number of carbons (36) match perfectly. This has been further confirmed when we recorded 13C NMR spectrum of the compound 27 in DMSO-d6, which showed 36 signals for 36 carbons. From these studies it looks clear that one of the quaternary aliphatic carbons (probably C-3 because it is benzylic, allylic, tertiary and α to oxygen) appears at downfield region (beyond d 113.00).
77. We thank one of the referees for suggestions in understanding the stereochemistry of these compounds.
78. Structure of this compound 28 was assigned in analogy with that of 27.