Indolo quinazoline synthesis

Domon, L., Le Coeur, C., Grelard, A., Thiery, V. and Besson, T., Efficient modified von Niementowski synthesis of novel derivatives of 5a, 14b, 15-triazabenzo [a ]indeno[ 1,2-c]anthracen-5-one from indolo [l,2-c]quinazoline, Tetrahedron Lett., 2001, 42, 6671-6674. 

Nitrogen Heterocycles.- Reactions of iminophosphoranes have been used to prepare a wide range of heterocycles. Examples of compounds prepared by intramolecular aza-Wittig reactions include 3,4-dihydroquinazolines (191) and quinazolines (192), quinazoline derivatives (e.g. 193),pyrrolo( 1,2-a)quinoxalines (194), indolo[3,2-clquinolines (195), and indolo[l,2-c]quinazolines (196),"8 imidazolinones (197),"9 quinazolinones (198),"9, 120 pyrido[2,3-d]pyrimidine derivatives (199), 21 and 4,5-dihydropyrazolo(3,4-d]pyrimidine derivatives (200). 22 Tributyl(cyclohepta-1,3,5-trienylimino)phosphorane (201), prepared by thermal isomerization of the 2,4,6-derivative, reacts with a,p-unsaturated ketones to give 9H-cyclohepta[b]pyridine derivatives (202). 23 a synthesis of (2,4)pyridinophanes (204) by the reaction of N-vinyliminophosphoranes (203) with a,P-unsaturated ketones has been reported. 24... 

The simple synthesis of antimycotic alkaloid tryptanthrin 17 via the quinazolinone annelation is summarized also in Scheme 18. Quinazolinone annelation of commercially available isatin 84 under the shown conditions gave 17 in 43% overall yield (Scheme 18) [222]. As the second route, oxindole 82 was annelated to indolo[2,l-fo]quinazolin-12(6ff)-one 83, which could be converted to 17 by air-oxidation but only in the modest yield [222]. Recently an efficient procedure for synthesis 17,16 and luotonin A (26), etc. has been reported using cyclocondensation of iminochloride and methylanthranylate, followed by further manipulations by Jahng et al. [229]. Several known attractive routes to 17 involves cyclocondensation of isatin with isatoic anhydride by Mitscher et al. [230], (Ru)3(CO)i2-catalyzed reductive J -heterocycUzation by Watanabe et al. [182,223]. 

A convenient and clean water-mediated synthesis of a series of indolo[l,2-c] quinazoline derivatives was reported using alternative nonconventional energy sources. The products are obtained in shorter times with excellent yields (78-89 %) from the MCR of 2-arrrinobenzimidazole, malononitrile, and carbonyl compourtds [55]. In their research, 2-(2-halophenyl)-lH-indoles arrd (aryl)methanamines were adopted as raw rrraterials to generate corresponding Schiff base via the Ullrrrarm reaction. Thert, gas as oxidarrt, 3 equiv K COj as base, and 10 mol% Cu(OAc)2 as catalyst were revealed as the optimum conditions to conduct aerobic oxidative C-H amination under solvent-free conditions or water (Scheme 13.14). 

Rohini R, Muralidhar Reddy P, Shanker K, Hu A, Ravinder V (2010) Antimierobial study of newly synthesized 6-substituted indolo[l,2-e]quinazolines. Eur J Med Chem 45 1200-1205 Antipenko L, Karpenko A, Kovalenko S, Katsev A, Komarovska-Porokhnyavets E, Novikov V, Chekotilo A (2009) Synthesis of new 2-thio-[l,2,4]triazolo[l,5-e] quinazoline derivatives and its antimicrobial activity. Chem Pharm Bull 57 580-585... 

He P, Nie YB, Wu J, Ding MW (2011) Unexpected synthesis of indolo[l,2-c] quinazolines by a sequential ugi 4CC-Staudinger-aza-Wittig-nucleophihc addition reaction. Oig Biomol Chem 9 1429 1436... 

Molina P, Alajarin M, Vidal A (1990) New methodology for the preparation of pyrrole and indole derivatives via iminophosphoranes synthesis of pyrrolo[l,2-fl]quinoxalines, indolo[3,2-c] quinolines and indolo[l,2-c]quinazolines. Tetrahedron 46(3) 1063-1078. doi 10.1016/80040-4020(01)81384-3... 

Zou, Zhang et cd. developed an efficient Cu(OAc)2-catalyzed synthesis of indolo[l,2-c]quinazoline derivatives using environmentally friendly air as the oxidant (Scheme 8.104). Various indolo[l,2-c]quinazoline derivatives could be generated from readily available 2-(2-halophenyl)-LW-indoles and (aryl)methanamines in moderate to good yields via C(sp )-H bond activation [178]. 

Compounds in which other heterocyclic rings (pyrazoles, isoxazoles, imidazoles ) are fused to thiopyrans have been described. The interesting thiazolium salts (56) were prepared by allowing the betaines (55) to react with 4-thioxothiazolidin-2-ones. Application of the Fischer indole synthesis and the Friedlander reaction to tetrahydrothiopyran-3-one led to the exported indolo-and quinolino-derivatives. Ring closure of (57) under acidic conditions afforded the rearranged product (58). Syntheses of benzothiopyrano[4,3,2-flfe]-quinazolines (59) from 1-amino-thioxanthones and of their S- and 7V-oxides have been described. ... 

Staskun, B. and Wolfe, J. E, New approach to the Indolo(2,l-fo]quinazoline ring system by cycliza-tion of 3(o-chlorophenyl)-2-methyl-4(3Ff)quinazolinone and its m-isomer synthesis of the antibiotic tryptanthrin, S. Afr. J. Chem., 45, 5,1992. 

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