Application of organolithium in organic synthesis: A simple and convenient procedure for the synthesis of more complex 6-substituted 3H-quinazolin-4-ones

Monatshefte fur Chemie

Volumn 135, Issue 3, 2004, Pages 323-331

  El Hiti, Gamal A ^a,b  

^a Tanta University   (Egypt)

^b SWANSEA UNIVERSITY   (United Kingdom)

Author keywords

3H Quinazolin 4 one; Bromine lithium exchange; Dilithio reagent; Electrophiles; Nucleophilic addition

Indexed keywords

2 BUTYL 1,2 DIHYDRO 3H QUINAZOLIN 4 ONE; 2 BUTYL 6 METHYL 1,2 DIHYDRO 3H QUINAZOLIN 4 ONE; 2 TERT BUTYL 1,2 DIHYDRO 3H QUINAZOLIN 4 ONE; 2 TERT BUTYL 6 METHYL 1,2 DIHYDRO 3H QUINAZOLIN 4 ONE; 2,6 DIMETHYL 1,2 DIHYDRO 3H QUINAZOLIN 4 ONE; 6 (1 HYDROXY 1 METHYLPENTYL) 3H QUINAZOLIN 4 ONE; 6 (1 HYDROXYCYCLOHEXYL) 3H QUINAZOLIN 4 ONE; 6 (DIISOPROPYLDITHIOCARBAMOYL) 3H QUINAZOLIN 4 ONE; 6 (HYDROXYDIPHENYLMETHYL) 3H QUINAZOLIN 4 ONE; 6 (HYDROXYPHENYLMETHYL) 3H QUINAZOLIN 4 ONE; 6 (PHENYLAMINOTHIOCARBONYL) 3H QUINAZOLIN 4 ONE; 6 [HYDROXY(4 METHOXYPHENYL)METHYL] 3H QUINAZOLIN 4 ONE; 6 ETHYL 3H QUINAZOLIN 4 ONE; 6,6' (1,3 PROPANEDIYL)BIS(3H QUINAZOLIN 4 ONE); QUINAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; LITHIATION;

EID: 1642359945     PISSN: 00269247     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00706-003-0110-5     Document Type: Article

References (50)

1. See for example: Choppin S, Gros P, Fort Y (2000) Org Lett 2: 803; Kondo Y, Asai M, Miura T, Uchiyama M, Sakamoto T (2001) Org Lett 3: 13; Toudic F, Plé N, Turck A, Quéguiner G (2002) Tetrahedron 58: 283; Rhonnstad P, Wensbo D (2002) Tetrahedron Lett 43: 3137; Mukherjee C, De A (2002) Synlett 325; Cuperly D, Gros P, Fort Y (2002) J Org Chem 67: 238; Gros P, Louërat F, Fort Y (2002) Org Lett 4: 1759; Bunch L, Krogsgaard-Larsen P, Madsen U (2002) J Org Chem 67: 2375; Gros P, Choppin S, Mathieu J, Fort Y (2002) J Org Chem 67: 234; Gros P, Choppin S, Fort Y (2003) J Org Chem 68: 2243; Katritzky AR, Manju K, Steel PJ (2003) J Org Chem 68: 407
2. See for example: Choppin S, Gros P, Fort Y (2000) Org Lett 2: 803; Kondo Y, Asai M, Miura T, Uchiyama M, Sakamoto T (2001) Org Lett 3: 13; Toudic F, Plé N, Turck A, Quéguiner G (2002) Tetrahedron 58: 283; Rhonnstad P, Wensbo D (2002) Tetrahedron Lett 43: 3137; Mukherjee C, De A (2002) Synlett 325; Cuperly D, Gros P, Fort Y (2002) J Org Chem 67: 238; Gros P, Louërat F, Fort Y (2002) Org Lett 4: 1759; Bunch L, Krogsgaard-Larsen P, Madsen U (2002) J Org Chem 67: 2375; Gros P, Choppin S, Mathieu J, Fort Y (2002) J Org Chem 67: 234; Gros P, Choppin S, Fort Y (2003) J Org Chem 68: 2243; Katritzky AR, Manju K, Steel PJ (2003) J Org Chem 68: 407
3. See for example: Choppin S, Gros P, Fort Y (2000) Org Lett 2: 803; Kondo Y, Asai M, Miura T, Uchiyama M, Sakamoto T (2001) Org Lett 3: 13; Toudic F, Plé N, Turck A, Quéguiner G (2002) Tetrahedron 58: 283; Rhonnstad P, Wensbo D (2002) Tetrahedron Lett 43: 3137; Mukherjee C, De A (2002) Synlett 325; Cuperly D, Gros P, Fort Y (2002) J Org Chem 67: 238; Gros P, Louërat F, Fort Y (2002) Org Lett 4: 1759; Bunch L, Krogsgaard-Larsen P, Madsen U (2002) J Org Chem 67: 2375; Gros P, Choppin S, Mathieu J, Fort Y (2002) J Org Chem 67: 234; Gros P, Choppin S, Fort Y (2003) J Org Chem 68: 2243; Katritzky AR, Manju K, Steel PJ (2003) J Org Chem 68: 407
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5. See for example: Choppin S, Gros P, Fort Y (2000) Org Lett 2: 803; Kondo Y, Asai M, Miura T, Uchiyama M, Sakamoto T (2001) Org Lett 3: 13; Toudic F, Plé N, Turck A, Quéguiner G (2002) Tetrahedron 58: 283; Rhonnstad P, Wensbo D (2002) Tetrahedron Lett 43: 3137; Mukherjee C, De A (2002) Synlett 325; Cuperly D, Gros P, Fort Y (2002) J Org Chem 67: 238; Gros P, Louërat F, Fort Y (2002) Org Lett 4: 1759; Bunch L, Krogsgaard-Larsen P, Madsen U (2002) J Org Chem 67: 2375; Gros P, Choppin S, Mathieu J, Fort Y (2002) J Org Chem 67: 234; Gros P, Choppin S, Fort Y (2003) J Org Chem 68: 2243; Katritzky AR, Manju K, Steel PJ (2003) J Org Chem 68: 407
6. See for example: Choppin S, Gros P, Fort Y (2000) Org Lett 2: 803; Kondo Y, Asai M, Miura T, Uchiyama M, Sakamoto T (2001) Org Lett 3: 13; Toudic F, Plé N, Turck A, Quéguiner G (2002) Tetrahedron 58: 283; Rhonnstad P, Wensbo D (2002) Tetrahedron Lett 43: 3137; Mukherjee C, De A (2002) Synlett 325; Cuperly D, Gros P, Fort Y (2002) J Org Chem 67: 238; Gros P, Louërat F, Fort Y (2002) Org Lett 4: 1759; Bunch L, Krogsgaard-Larsen P, Madsen U (2002) J Org Chem 67: 2375; Gros P, Choppin S, Mathieu J, Fort Y (2002) J Org Chem 67: 234; Gros P, Choppin S, Fort Y (2003) J Org Chem 68: 2243; Katritzky AR, Manju K, Steel PJ (2003) J Org Chem 68: 407
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20. See for example: Abdel-Megeed MF, Aly YL, Saleh MA, Abdo IM, El-Hiti GA, Smith K (1995) Sulfur Lett 19: 129; Abdo MA, Zeid IF, El-Hit GA, Mahmoud OE (1999) Indian J Chem 38B: 850; El-Hiti GA, Abdel-Megeed MF, Mahmoud YA-G (2000) Indian J Chem 39B: 368; Abdel-Megeed MF, El-Hiti GA, Abdo MA, Saleh MA (2000) Rev Roum Chim 45: 545; El-Hiti GA, Abdel-Megeed MF, Zied TM (2002) Indian J Chem 41B: 1519; El-Hiti GA (2003) Monatsh Chem 134: 837
21. See for example: Abdel-Megeed MF, Aly YL, Saleh MA, Abdo IM, El-Hiti GA, Smith K (1995) Sulfur Lett 19: 129; Abdo MA, Zeid IF, El-Hit GA, Mahmoud OE (1999) Indian J Chem 38B: 850; El-Hiti GA, Abdel-Megeed MF, Mahmoud YA-G (2000) Indian J Chem 39B: 368; Abdel-Megeed MF, El-Hiti GA, Abdo MA, Saleh MA (2000) Rev Roum Chim 45: 545; El-Hiti GA, Abdel-Megeed MF, Zied TM (2002) Indian J Chem 41B: 1519; El-Hiti GA (2003) Monatsh Chem 134: 837
22. See for example: Abdel-Megeed MF, Aly YL, Saleh MA, Abdo IM, El-Hiti GA, Smith K (1995) Sulfur Lett 19: 129; Abdo MA, Zeid IF, El-Hit GA, Mahmoud OE (1999) Indian J Chem 38B: 850; El-Hiti GA, Abdel-Megeed MF, Mahmoud YA-G (2000) Indian J Chem 39B: 368; Abdel-Megeed MF, El-Hiti GA, Abdo MA, Saleh MA (2000) Rev Roum Chim 45: 545; El-Hiti GA, Abdel-Megeed MF, Zied TM (2002) Indian J Chem 41B: 1519; El-Hiti GA (2003) Monatsh Chem 134: 837
23. See for example: Abdel-Megeed MF, Aly YL, Saleh MA, Abdo IM, El-Hiti GA, Smith K (1995) Sulfur Lett 19: 129; Abdo MA, Zeid IF, El-Hit GA, Mahmoud OE (1999) Indian J Chem 38B: 850; El-Hiti GA, Abdel-Megeed MF, Mahmoud YA-G (2000) Indian J Chem 39B: 368; Abdel-Megeed MF, El-Hiti GA, Abdo MA, Saleh MA (2000) Rev Roum Chim 45: 545; El-Hiti GA, Abdel-Megeed MF, Zied TM (2002) Indian J Chem 41B: 1519; El-Hiti GA (2003) Monatsh Chem 134: 837
24. See for example: Abdel-Megeed MF, Aly YL, Saleh MA, Abdo IM, El-Hiti GA, Smith K (1995) Sulfur Lett 19: 129; Abdo MA, Zeid IF, El-Hit GA, Mahmoud OE (1999) Indian J Chem 38B: 850; El-Hiti GA, Abdel-Megeed MF, Mahmoud YA-G (2000) Indian J Chem 39B: 368; Abdel-Megeed MF, El-Hiti GA, Abdo MA, Saleh MA (2000) Rev Roum Chim 45: 545; El-Hiti GA, Abdel-Megeed MF, Zied TM (2002) Indian J Chem 41B: 1519; El-Hiti GA (2003) Monatsh Chem 134: 837
25. Smith K, El-Hiti GA, Hamilton A (1998) J Chem Soc Perkin Trans 1: 4041; Smith K, El-Hiti GA, Pritchard GJ, Hamilton A (1999) J Chem Soc Perkin Trans 1: 2299; Smith K, El-Hiti GA, Shukla AP (1999) J Chem Soc Perkin Trans 1: 2305; Smith K, El-Hiti GA, Hawes AC (1999) Synlett 945; Smith K, El-Hiti GA, Hawes AC (2003) Synthesis: 2047
26. Smith K, El-Hiti GA, Hamilton A (1998) J Chem Soc Perkin Trans 1: 4041; Smith K, El-Hiti GA, Pritchard GJ, Hamilton A (1999) J Chem Soc Perkin Trans 1: 2299; Smith K, El-Hiti GA, Shukla AP (1999) J Chem Soc Perkin Trans 1: 2305; Smith K, El-Hiti GA, Hawes AC (1999) Synlett 945; Smith K, El-Hiti GA, Hawes AC (2003) Synthesis: 2047
27. Smith K, El-Hiti GA, Hamilton A (1998) J Chem Soc Perkin Trans 1: 4041; Smith K, El-Hiti GA, Pritchard GJ, Hamilton A (1999) J Chem Soc Perkin Trans 1: 2299; Smith K, El-Hiti GA, Shukla AP (1999) J Chem Soc Perkin Trans 1: 2305; Smith K, El-Hiti GA, Hawes AC (1999) Synlett 945; Smith K, El-Hiti GA, Hawes AC (2003) Synthesis: 2047
28. Smith K, El-Hiti GA, Hamilton A (1998) J Chem Soc Perkin Trans 1: 4041; Smith K, El-Hiti GA, Pritchard GJ, Hamilton A (1999) J Chem Soc Perkin Trans 1: 2299; Smith K, El-Hiti GA, Shukla AP (1999) J Chem Soc Perkin Trans 1: 2305; Smith K, El-Hiti GA, Hawes AC (1999) Synlett 945; Smith K, El-Hiti GA, Hawes AC (2003) Synthesis: 2047
29. Smith K, El-Hiti GA, Hamilton A (1998) J Chem Soc Perkin Trans 1: 4041; Smith K, El-Hiti GA, Pritchard GJ, Hamilton A (1999) J Chem Soc Perkin Trans 1: 2299; Smith K, El-Hiti GA, Shukla AP (1999) J Chem Soc Perkin Trans 1: 2305; Smith K, El-Hiti GA, Hawes AC (1999) Synlett 945; Smith K, El-Hiti GA, Hawes AC (2003) Synthesis: 2047
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32. Smith K, El-Hiti GA, Abdo MA, Abdel-Megeed MF (1995) J Chem Soc Perkin Trans 1: 1029; Smith K, El-Hiti GA, Abdel-Megeed MF, Abdo MA (1996) J Org Chem 61: 647; Smith K, El-Hiti GA, Abdel-Megeed MF, Abdo MA (1996) J Org Chem 61: 656; El-Hiti GA (2000) Heterocycles 53: 1839; Smith K, El-Hiti GA, Abdel-Megeed MF (2003) Russ J Org Chem 39: 430
33. Smith K, El-Hiti GA, Abdo MA, Abdel-Megeed MF (1995) J Chem Soc Perkin Trans 1: 1029; Smith K, El-Hiti GA, Abdel-Megeed MF, Abdo MA (1996) J Org Chem 61: 647; Smith K, El-Hiti GA, Abdel-Megeed MF, Abdo MA (1996) J Org Chem 61: 656; El-Hiti GA (2000) Heterocycles 53: 1839; Smith K, El-Hiti GA, Abdel-Megeed MF (2003) Russ J Org Chem 39: 430
34. Smith K, El-Hiti GA, Abdo MA, Abdel-Megeed MF (1995) J Chem Soc Perkin Trans 1: 1029; Smith K, El-Hiti GA, Abdel-Megeed MF, Abdo MA (1996) J Org Chem 61: 647; Smith K, El-Hiti GA, Abdel-Megeed MF, Abdo MA (1996) J Org Chem 61: 656; El-Hiti GA (2000) Heterocycles 53: 1839; Smith K, El-Hiti GA, Abdel-Megeed MF (2003) Russ J Org Chem 39: 430
35. Smith K, El-Hiti GA, Abdel-Megeed MF, Abdo MA (1999) Collect Czech Chem Commun 64: 515
36. See for example: Honda G, Tabata M, Tsuda M (1979) Planta Med 37: 172; Johne S (1982) Prog Drug Res 26: 259; Johne S (1986) The Alkaloids 29: 99; Schlecker R, Treiber HJ, Behl B, Hofmann HP (1994) Ger Offen 4 241 563 (1994) Chem Abstr 121: 230787h; Barker AJ (1995) Eur P, 635 498 (1995) Chem Abstr 122: 214099a; Barker AJ, Johnstine C (1997) PCT Int Appl WO 300 44 (1997) Chem Abstr 127: 220671a; Hour M-J, Huang L-J, Kuo S-C, Xia Y, Bastow K, Nakanishi Y, Hamel E, Lee K-H (2000) J Med Chem 43: 4479; Ho N, Harapanhalli RS, Dahman BA, Chen K, Wang K (2002) Bioconjugate Chem 13: 357
37. See for example: Honda G, Tabata M, Tsuda M (1979) Planta Med 37: 172; Johne S (1982) Prog Drug Res 26: 259; Johne S (1986) The Alkaloids 29: 99; Schlecker R, Treiber HJ, Behl B, Hofmann HP (1994) Ger Offen 4 241 563 (1994) Chem Abstr 121: 230787h; Barker AJ (1995) Eur P, 635 498 (1995) Chem Abstr 122: 214099a; Barker AJ, Johnstine C (1997) PCT Int Appl WO 300 44 (1997) Chem Abstr 127: 220671a; Hour M-J, Huang L-J, Kuo S-C, Xia Y, Bastow K, Nakanishi Y, Hamel E, Lee K-H (2000) J Med Chem 43: 4479; Ho N, Harapanhalli RS, Dahman BA, Chen K, Wang K (2002) Bioconjugate Chem 13: 357
38. See for example: Honda G, Tabata M, Tsuda M (1979) Planta Med 37: 172; Johne S (1982) Prog Drug Res 26: 259; Johne S (1986) The Alkaloids 29: 99; Schlecker R, Treiber HJ, Behl B, Hofmann HP (1994) Ger Offen 4 241 563 (1994) Chem Abstr 121: 230787h; Barker AJ (1995) Eur P, 635 498 (1995) Chem Abstr 122: 214099a; Barker AJ, Johnstine C (1997) PCT Int Appl WO 300 44 (1997) Chem Abstr 127: 220671a; Hour M-J, Huang L-J, Kuo S-C, Xia Y, Bastow K, Nakanishi Y, Hamel E, Lee K-H (2000) J Med Chem 43: 4479; Ho N, Harapanhalli RS, Dahman BA, Chen K, Wang K (2002) Bioconjugate Chem 13: 357
39. See for example: Honda G, Tabata M, Tsuda M (1979) Planta Med 37: 172; Johne S (1982) Prog Drug Res 26: 259; Johne S (1986) The Alkaloids 29: 99; Schlecker R, Treiber HJ, Behl B, Hofmann HP (1994) Ger Offen 4 241 563 (1994) Chem Abstr 121: 230787h; Barker AJ (1995) Eur P, 635 498 (1995) Chem Abstr 122: 214099a; Barker AJ, Johnstine C (1997) PCT Int Appl WO 300 44 (1997) Chem Abstr 127: 220671a; Hour M-J, Huang L-J, Kuo S-C, Xia Y, Bastow K, Nakanishi Y, Hamel E, Lee K-H (2000) J Med Chem 43: 4479; Ho N, Harapanhalli RS, Dahman BA, Chen K, Wang K (2002) Bioconjugate Chem 13: 357
40. See for example: Honda G, Tabata M, Tsuda M (1979) Planta Med 37: 172; Johne S (1982) Prog Drug Res 26: 259; Johne S (1986) The Alkaloids 29: 99; Schlecker R, Treiber HJ, Behl B, Hofmann HP (1994) Ger Offen 4 241 563 (1994) Chem Abstr 121: 230787h; Barker AJ (1995) Eur P, 635 498 (1995) Chem Abstr 122: 214099a; Barker AJ, Johnstine C (1997) PCT Int Appl WO 300 44 (1997) Chem Abstr 127: 220671a; Hour M-J, Huang L-J, Kuo S-C, Xia Y, Bastow K, Nakanishi Y, Hamel E, Lee K-H (2000) J Med Chem 43: 4479; Ho N, Harapanhalli RS, Dahman BA, Chen K, Wang K (2002) Bioconjugate Chem 13: 357
41. See for example: Honda G, Tabata M, Tsuda M (1979) Planta Med 37: 172; Johne S (1982) Prog Drug Res 26: 259; Johne S (1986) The Alkaloids 29: 99; Schlecker R, Treiber HJ, Behl B, Hofmann HP (1994) Ger Offen 4 241 563 (1994) Chem Abstr 121: 230787h; Barker AJ (1995) Eur P, 635 498 (1995) Chem Abstr 122: 214099a; Barker AJ, Johnstine C (1997) PCT Int Appl WO 300 44 (1997) Chem Abstr 127: 220671a; Hour M-J, Huang L-J, Kuo S-C, Xia Y, Bastow K, Nakanishi Y, Hamel E, Lee K-H (2000) J Med Chem 43: 4479; Ho N, Harapanhalli RS, Dahman BA, Chen K, Wang K (2002) Bioconjugate Chem 13: 357
42. See for example: Honda G, Tabata M, Tsuda M (1979) Planta Med 37: 172; Johne S (1982) Prog Drug Res 26: 259; Johne S (1986) The Alkaloids 29: 99; Schlecker R, Treiber HJ, Behl B, Hofmann HP (1994) Ger Offen 4 241 563 (1994) Chem Abstr 121: 230787h; Barker AJ (1995) Eur P, 635 498 (1995) Chem Abstr 122: 214099a; Barker AJ, Johnstine C (1997) PCT Int Appl WO 300 44 (1997) Chem Abstr 127: 220671a; Hour M-J, Huang L-J, Kuo S-C, Xia Y, Bastow K, Nakanishi Y, Hamel E, Lee K-H (2000) J Med Chem 43: 4479; Ho N, Harapanhalli RS, Dahman BA, Chen K, Wang K (2002) Bioconjugate Chem 13: 357
43. See for example: Honda G, Tabata M, Tsuda M (1979) Planta Med 37: 172; Johne S (1982) Prog Drug Res 26: 259; Johne S (1986) The Alkaloids 29: 99; Schlecker R, Treiber HJ, Behl B, Hofmann HP (1994) Ger Offen 4 241 563 (1994) Chem Abstr 121: 230787h; Barker AJ (1995) Eur P, 635 498 (1995) Chem Abstr 122: 214099a; Barker AJ, Johnstine C (1997) PCT Int Appl WO 300 44 (1997) Chem Abstr 127: 220671a; Hour M-J, Huang L-J, Kuo S-C, Xia Y, Bastow K, Nakanishi Y, Hamel E, Lee K-H (2000) J Med Chem 43: 4479; Ho N, Harapanhalli RS, Dahman BA, Chen K, Wang K (2002) Bioconjugate Chem 13: 357
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45. Stevenson TM, Kazmierczak F, Leonard NJ (1986) J Org Chem 51: 616; Baker BR, Schaub RE, Joseph JP, McEvoy FJ, Williams JH (1952) J Org Chem 17: 149
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