Simple and new protocol for the synthesis of novel (z)-3- arylidenebenzothiazepin-4-ones using Baylis-Hillman derivatives

Synthetic Communications

Volumn 38, Issue 20, 2008, Pages 3406-3413

  Bakthadoss, Manickam ^a   Murugan, Gandhi ^a  

^a UNIVERSITY OF MADRAS   (India)

Author keywords

2 Amino thiophenol; Baylis Hillman reaction; Benzothiazepinones; Diltiazem; p toluenesulfonic acid; Thiazesim

Indexed keywords

2 AMINOTHIOPHENOL; 3 (2 METHYLBENZYLIDENE) 2,3 DIHYDROBENZO[B][1,4]THIAZEPIN 4(5H)ONE; 3 (4 ETHYLBENZYLIDENE) 2,3 DIHYDROBENZO[B][1,4]THIAZEPIN 4(5H)ONE; 3 (4 METHYLBENZYLIDENE) 2,3 DIHYDROBENZO[B][1,4]THIAZEPIN 4(5H)ONE; 3 BENZYLIDENE 2,3 DIHYDROBENZO[B][1,4]THIAZEPIN 4(5H)ONE; BENZOTHIAZEPINE DERIVATIVE; NITROGEN; SULFONIC ACID DERIVATIVE; SULFUR; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; BAYLIS HILLMAN REACTION; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG STRUCTURE; DRUG SYNTHESIS; INFRARED SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE;

EID: 53149088566     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802138249     Document Type: Article

References (28)

1. Basavaiah, D.; Venkateswara Rao, K.; Reddy, R. J. The Baylis-Hilman reaction: A novel source of attraction, opportunities, and challenges in synthetic chemistry. Chem. Soc. Rev. 2007, 36, 1581-1588.
2. Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Recent advances in the Baylis-Hilman reaction and applications. Chem. Rev. 2003, 103, 811-891.
3. Ciganek, E. Organic Reactions; L. A. Paquette (Ed.); Wiley: New York, 1997; vol. 51, pp. 201-350.
4. (a) Aroyan, C. E.; Vasbinder, M. M.; Miller, S. J. Dual catalyst control in the enantioselective intramolecular Morita-Baylis-Hillman reaction. Org. Lett. 2005, 7, 3849-3851;
5. (b) Kabalka, G. W.; Dong, G.; Venkataiah, B.; Chen, C. Palladium-catalyzed cross-coupling of Baylis-Hillman acetate adducts with organosilanes. J. Org. Chem. 2005, 70, 9207-9210;
6. (c) Krafft, M. E.; Haxell, T. F. N. Organomediated Morita-Baylis-Hillman cyclization reactions. J. Am. Chem. Soc. 2005, 127, 10168-10169.
7. (a) Basavaiah, D.; Aravindu, K. The Baylis-Hillman acetates as a valuable source for one-pot multistep synthesis: A facile synthesis of functionalized tri-/tetracyclic frameworks containing azocine moiety. Org. Lett. 2007, 9, 2453-2456;
8. (b) Basavaiah, D.; Mallikarjuna Reddy, R.; Kumaragurubaran, N.; Sharada, D. S. Applications of Baylis-Hillman chemistry: One-pot convenient synthesis of functionalized (1H)-quinol-2-ones and quinolines. Tetrahedron 2002, 58, 3693-3697;
9. (c) Shanmugan, P.; Viswambharan, B.; Madhavan, S. Synthesis of novel functionalized 3-spiropyrrolizidine and 3-spiropyrrolidine oxindoles from Baylis-Hillman adducts of isatin and heteroaldehydes with azomethine ylides via [3 + 2]-cycloaddition. Org. Lett. 2007, 9, 4095-4098;
10. (d) Dep, I.; Dadwal, M.; Mobin, S. M.; Namboothiri, I. N. N. Hydroxyalkylation of conjugated nitroalkenes with activated nonenolizable carbonyl compounds. Org. Lett. 2006, 8, 1201-1204.
11. Gonzalez, A. G.; Silva, M. H.; Padron, J. I.; Leon, F.; Reyes, E.; Alvarezmon, M.; Pivel, J. P.; Quintana, J.; Estevez, F.; Bermejo, J. Synthesis and antiproliferative activity of a new compound containing an a-methylene-clactone group. J. Med. Chem. 2002, 45, 2358-2361.
12. Mergott, D. J.; Frank, S. A.; Roush, W. R. Application of the intramolecular vinylogous Morita-Baylis-Hillman reaction toward the synthesis of the spinosyn, a tricyclic nucleus. Org. Lett. 2002, 4, 3157-3160.
13. Trost, B. M.; Thiel, O. R.; Tsui, H. C. DYKAT of Baylis-Hillman adducts: Concise total synthesis of furaquinocin E. J. Am. Chem. Soc. 2002, 124, 11616-11617.
14. Loh, T. P.; Cao, G. Q.; Pei, J. Studies towards total synthesis of antillatoxin: Synthesis of C1-C11 fragment. Tetrahedron Lett. 1998, 39, 1457-1460.
15. (a) Amblard, M.; Daffix, I.; Bedos, P.; Berge, G.; Pruneau, D.; Paquet, J. L.; Luccarini, J. M.; Belichard, P.; Dodey, P.; Martinez, J. Design and synthesis of potent bradykinin agonists containing a benzothiazepine moiety. J. Med. Chem. 1999, 42, 4185-4192;
16. 2 receptor agonists containing constrained dipeptidemimics. J. Med. Chem. 1999, 42, 4193-4201;
17. (c) Robl, J. A.; Sun, C. Q.; Stevenson, J.; Ryono, D. E.; Simpkins, L. M.; Cimarusti, M. P.; Dejneka, T.; Slusarchyk, W. A.; Chao, S.; Stratton, L.; Misra, R. N.; Bednarz, M. S.; Asaad, M. M.; Cheung, H. S.; Abboa-Offei, B. E.; Smith, P. L.; Mathers, P. D.; Fox, M.; Schaeffer, T. R.; Seymour, A. A.; Trippodo, N. C. Dual metalloprotease inhibitors: Mercaptoacetyl-based fused heterocyclic dipeptide mimetics as inhibitors of angiotensin-converting enzyme and neutral endopeptidase. J. Med. Chem. 1997, 40, 1570-1577.
18. Boschelli, D. H.; Connor, D. T.; Kramer, J. B.; Unangst, P. C. Method for treating inflammatory disease in humans. U.S. Patent 5,489,586, Dec. 12, 1994.
19. Watson, K. G.; Fung, Y. M.; Gredley, M.; Bird, G. J.; Jackson, W. R.; Gountzos, H.; Matthews, B. R. Asymmetric syntheses of (+)-diltiazem hydrochloride. J. Chem. Soc., Chem. Commun. 1990, 1018-1019.
20. Schwartz, A.; Madan, P. B.; Mohacai, E.; O'Brien, J. P.; Todaro, L. J.; Coffen, D. L. Enantioselective synthesis of calcium channel blockers of the diltiazem group. J. Org. Chem. 1992, 57, 851-856.
21. Lohray, B. B.; Jayachandran, B.; Bhushan, V.; Nandanan, E.; Ravindranathan, T. Anchimeric assisted unprecedented SNi-type cleavage of cyclic sulfite: Application in the synthesis of the calcium channel blocker diltiazem. J. Org. Chem. 1995, 60, 5983-5985.
22. Yamada, S.; Mori, Y.; Morimatsu, K.; Ishizu, Y.; Ozaki, Y.; Yoshioka, R.; Nakatani, T.; Seko, H. Asymmetric reduction of a 1,5-benzothiazepine derivative with sodium borohydride-(S)-α-amino acids: An efficient synthesis of a key intermediate of diltiazem. J. Org. Chem. 1996, 61, 8586-8590.
23. 2+ antagonistic activity of diltiazem metabolites. J. Med. Chem. 1992, 35, 3246-3253.
24. Krapcho, J.; Turk, C. F. Substituted 2,3-dihydro-1,5-benzothiazepin- 4(5H)-one and related compounds, II: A new class of antidepressants. J. Med. Chem. 1966, 9, 191-195.
25. Basavaiah, D.; Bakthadoss, M.; Pandiaraju, S. A new protocol for the syntheses of (E)-3-benzylidenechroman-4-ones: A simple synthesis of the methyl ether of bonducellin. Chem. Commun. 1998, 1639-1640.
26. (a) Basavaiah, D.; Bakthadoss, M.; Jayapal Reddy, G. The first intramolecular Friedel-Crafts reaction of Baylis-Hillman adducts: Synthesis of functionalized indene and indane derivatives. Synthesis 2001, 6, 919-923;
27. (b) Basavaiah, D.; Bakthadoss, M.; Jayapal Reddy, G. Tandem construction of carbon-carbon and carbon-oxygen bonds in the Baylis-Hillman chemistry: Synthesis of functionalized dl-bis-allyl ethers. Synth. Commun. 2002, 32, 689-697.
28. Bakthadoss, M.; Sivakumar, N.; Sivakumar, G.; Murugan, G. Highly regioand stereoselective synthesis of tricyclic frameworks using Baylis-Hillman derivatives. Tetrahedron. Lett. 2008, 49, 820-823.